4-(4-haloalkyl-3-thiobenzoyl)pyrazoles and use thereof as herbicides

ABSTRACT

A description is given of 4-(4-haloalkyl-3-thiobenzoyl)pyrazoles of the formula (I) and of their use as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), X, Y, R 1 , R 2 , R 3 , and R 4  are radicals such as hydrogen and organic radicals such as alkyl.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims priority to EP 10170238.9 filed Jul. 21, 2010,the content of which is incorporated herein by reference in itsentirety.

BACKGROUND

1. Field of the Invention

The invention relates to the technical field of herbicides, moreparticularly that of herbicides for the selective control of broadleafand grass weeds in crops of useful plants.

2. Description of Related Art

From various publications it is already known that certainbenzoylpyrazoles possess herbicidal properties. For instance, EP 0 352543, WO 00/03993, and WO 2008/125214 disclose benzoylpyrazolessubstituted by various radicals.

The herbicidal activity of the compounds known from these publications,however, is frequently inadequate. It is therefore an object of thepresent invention to provide herbicidally active compounds whoseherbicidal properties are improved as compared with those of thecompounds known from the prior art.

SUMMARY

It has now been found that certain 4-benzoylpyrazoles whose phenyl ringcarries a thio group in position 3 and a haloalkyl group in position 4are especially suitable as herbicides. The present invention firstlyprovides 4-(4-haloalkyl-3-thiobenzoyl)pyrazoles of the formula (I) orsalts thereof

in which

-   X is (C₁-C₄)-alkyl,-   Y is (C₁-C₄)-haloalkyl bar trifluoromethyl,-   R¹ is (C₁-C₄)-alkyl,-   R² is (C₁-C₄)-alkyl,-   R³ is hydrogen or (C₁-C₄)-alkyl,-   R⁴ is hydrogen, (C₁-C₆)-alkylsulfonyl,    (C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl,    thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl,    each of which is substituted by m identical or different radicals    from the group consisting of halogen, (C₁-C₄)-alkyl, and    (C₁-C₄)-alkoxy,-   m is 0, 1, 2 or 3, and-   n is 0, 1 or 2.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

Where R⁴ is hydrogen, the compounds of the invention of the formula (I)may exist in the form of different tautomeric structures, depending onexternal conditions, such as solvent and pH, as follows:

Depending on the nature of the substituents, the compounds of theformula (I) contain an acidic proton which can be removed by reactionwith a base. Examples of suitable bases include hydrides, hydroxides,and carbonates of lithium, sodium, potassium, magnesium, and calcium,and also ammonia and organic amines such as triethylamine and pyridine.In addition, salts may be formed by reaction with organic acids, such asformic acid or acetic acid, and with inorganic acids, such asphosphoric, hydrochloric or sulfuric acid. Such salts are likewiseprovided by the invention.

In the formula (I) and all subsequent formulae, alkyl radicals havingmore than two carbon atoms may be straight-chain or branched. Alkylradicals are, for example, methyl, ethyl, n- or iso-propyl, n-, iso-,tert- or 2-butyl, pentyl, hexyl, such as n-hexyl, iso-hexyl and1,3-dimethylbutyl. Halogen is fluorine, chlorine, bromine or iodine.

Where a group is substituted multiply by radicals, this means that thegroup in question is substituted by one or more identical or differentmembers from among the radicals specified.

Depending on the nature and attachment of the substituents, thecompounds of the formula (I) may be present in the form ofstereoisomers. Where, for example, one or more asymmetricallysubstituted carbon atoms or sulfoxides are present, then enantiomers anddiastereomers may occur. Stereoisomers may be obtained from the mixturesresulting from the preparation process by customary separation methods,such as by chromatographic separation methods, for example. It islikewise possible for stereoisomers to be prepared selectively throughdeployment of stereoselective reactions using optically active startingmaterials and/or auxiliaries. The invention also relates to all of thestereoisomers and mixtures thereof that are embraced by the formula (I)but not defined specifically.

Of particular interest are compounds of the formula (I) in which

-   X is (C₁-C₄)-alkyl,-   Y is (C₁-C₄)-haloalkyl of bar trifluoromethyl,-   R¹ is (C₁-C₄)-alkyl,-   R² is (C₁-C₄)-alkyl,-   R³ is hydrogen or (C₁-C₄)-alkyl,-   R⁴ is hydrogen, (C₁-C₆)-alkylsulfonyl,    (C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl,    thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl,    each of which is substituted by m identical or different radicals    from the group consisting of halogen, (C₁-C₄)-alkyl, and    (C₁-C₄)-alkoxy,-   m is 0, 1, 2 or 3, and-   n is 0, 1 or 2.

Preference is given to compounds of the formula (I) in which

-   X is (C₁-C₄)-alkyl,-   Y is trichloromethyl, difluoromethyl, dichlorofluoromethyl,    chlorodifluoromethyl, pentafluoroethyl or heptafluoroisopropyl,-   R¹ is (C₁-C₄)-alkyl,-   R² is (C₁-C₄)-alkyl,-   R³ is hydrogen or (C₁-C₄)-alkyl,-   R⁴ is hydrogen, n-propylsulfonyl, methoxyethylsulfonyl,    phenylsulfonyl, 4-methyl-phenylsulfonyl, or thiophenyl-2-sulfonyl,    and-   n is 0, 1 or 2.

Particular preference is given to compounds of the formula (I) in which

-   X is methyl,-   Y is difluoromethyl or pentafluoroethyl,-   R¹ is methyl,-   R² is methyl,-   R³ is hydrogen or methyl,-   R⁴ is hydrogen, and-   n is 1 or 2.

Very particular preference is given to compounds of the formula (I) inwhich

-   X is methyl,-   Y is pentafluoroethyl,-   R¹ is methyl,-   R² is methyl,-   R³ is hydrogen or methyl,-   R⁴ is hydrogen, and-   n is 1 or 2.

In all formulae given below, the substituents and symbols, unlessdefined otherwise, have the same meaning as described under formula (I).

Compounds of the invention in which R⁴ is hydrogen may be prepared, forexample, by the process, indicated in Scheme 1 and known from Acta Chem.Scand. 13 (1959), 1668-1670, by base-catalyzed reaction of a benzoylhalide (III) with a pyrazolone (II), or in accordance with the processindicated in Scheme 2 and known, for example, from EP-A 0 186 117, bybase-catalyzed reaction of a benzoyl halide (III) with a pyrazolone (II)and subsequent rearrangement. These processes are also known fromWO2005/122768.

The intermediate (IV) may also be prepared by direct reaction of abenzoic acid (IIIa) with a pyrazolone (II) with the addition of anactivating condensation agent such asN-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, forexample.

Compounds of the invention in which R⁴ has a definition other thanhydroxyl are usefully prepared from the compounds obtainable inaccordance with Scheme 1 or 2, by alkylation or acylation. Methods ofthis kind are fundamentally known to the skilled person and described inWO2005/122768, for example.

The pyrazolones of the formula (II) are available commercially or can beprepared in accordance with the process known to the skilled person anddescribed in EP-A 240 001, for example.

The benzoyl halides of the formula (III) are prepared from the benzoicacids of the formula (IIIa) by means, for example, of reaction withthionyl chloride.

The benzoic acids (IIIa) are obtainable via a series of synthetic stepsknown per se to the skilled person.

For example, the synthesis of benzoic acids carrying a trifluoromethylgroup as haloalkyl group in position 4 is known from WO 2008125214.Depending on the nature of the haloalkyl group, the processes describedtherein may be applied to the synthesis of the benzoic acids (IIIa).

A further possibility is the introduction of haloalkyl groups. Forexample, the introduction of a pentafluoroethyl group into position 4 ofa benzonitrile is described in WO 2006/43064 and US 2007/185058. Thebenzonitrile may be converted subsequently into the correspondingbenzoic acid (US 2007/185058). Also known is the substitution of theiodoaromatic compound by a haloalkyl group, a reaction which proceedsvia the corresponding haloalkyl copper compound (A. A. Kolomeitsev etal., J. Org. Chem. 2008, 73 (7), 2607.).

Alternatively, haloalkyl groups may also be generated from otherfunctional groups. A difluoromethyl group is accessible, for example,from the corresponding formyl group. A transformation of this kind isdescribed for 4-formylbenzonitrile by C. P. Andrieux et. al. (Journal ofthe American Chemical Society 1997 (119), 40, 9527). The correspondingbenzoic acid can then be generated from the product under basicconditions, for example (F. Mathey et. al., Tetrahedron 1975 (31),391.).

Further possibilities for synthetic access to benzoic acids that may beapplied to the synthesis of the benzoic acids (IIIa) are known from WO03/014071.

The sulfur atom in position 3 of the benzoyl group need not necessarilybe oxidized at the stage of the benzoic acid in order to generatecompounds with n=1 or 2; for example, an oxidation of this kind at thestage of the enol ester or of the 4-benzoyl-5-hydroxypyrazole may alsobe useful.

Benzoic acids of the formula (IIIa) are new and likewise provided by theinvention.

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the aforementioned reactions can also be preparedin a parallel manner, it being possible for this to take place in amanual, partly automated or completely automated manner. In thisconnection, it is, for example, possible to automate the reactionprocedure, the work-up or the purification of the products and/orintermediates. Overall, this is understood as meaning a procedure asdescribed, for example, by D. Tiebes in CombinatorialChemistry—Synthesis, Analysis, Screening (editor Gunther Jung), VerlagWiley 1999, on pages 1 to 34.

For the parallel reaction procedure and work-up, it is possible to use aseries of commercially available instruments, for example Calypsoreaction blocks from Barnstead International, Dubuque, Iowa 52004-0797,USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex,CB11 3AZ, England or MultiPROBE automated workstations from PerkinElmer, Waltham, Mass. 02451, USA. For the parallel purification ofcompounds of the formula (I) and salts thereof or of intermediatesproduced during the preparation, there are available, inter alia,chromatography apparatuses, for example from ISCO, Inc., 4700 SuperiorStreet, Lincoln, Nebr. 68504, USA.

The apparatuses listed lead to a modular procedure in which theindividual process steps are automated, but between the process stepsmanual operations have to be carried out. This can be circumvented byusing partly or completely integrated automation systems in which therespective automation modules are operated, for example, by robots.Automation systems of this type can be acquired, for example, fromCaliper, Hopkinton, Mass. 01748, USA.

The implementation of single or several synthesis steps can be supportedthrough the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described here, the preparation of compounds of theformula (I) and salts thereof can take place completely or partially bysolid-phase supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bonded to a synthesis resin.Solid-phase supported synthesis methods are sufficiently described inthe specialist literature, e.g. Barry A. Bunin in “The CombinatorialIndex”, Verlag Academic Press, 1998 and CombinatorialChemistry—Synthesis, Analysis, Screening (editor Gunther Jung), VerlagWiley, 1999. The use of solid-phase supported synthesis methods permitsa series of protocols known in the literature, which again can becarried out manually or in an automated manner. The reactions can becarried out, for example, by means of IRORI technology in microreactorsfrom Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.

Both on a solid phase and in liquid phase can the procedure ofindividual or several synthesis steps be supported through the use ofmicrowave technology. The specialist literature describes a series ofexperimental protocols, for example in Microwaves in Organic andMedicinal Chemistry (editors C. O. Kappe and A. Stadler), Verlag Wiley,2005.

The preparation according to the process described here producescompounds of the formula (I) and their salts in the form of substancecollections which are called libraries. The present invention alsoprovides libraries which comprise at least two compounds of the formula(I) and their salts.

The compounds of the formula (I) according to the invention (and/ortheir salts), hereinbelow also referred to together as “compoundsaccording to the invention”, have excellent herbicidal efficacy againsta broad spectrum of economically important monocotyledonous anddicotyledonous annual weed plants. The active compounds act efficientlyeven on perennial weeds which produce shoots from rhizomes, root stocksand other perennial organs and which are difficult to control.

The present invention therefore also relates to a method for controllingunwanted plants or for regulating the growth of plants, preferably incrops of plants, where one or more compound(s) according to theinvention is/are applied to the plants (for example harmful plants suchas monocotyledonous or dicotyledonous weeds or undesired crop plants),to the seeds (for example grains, seeds or vegetative propagules such astubers or shoot parts with buds) or to the area on which the plants grow(for example the area under cultivation). In this context, the compoundsaccording to the invention can be applied for example pre-sowing (ifappropriate also by incorporation into the soil), pre-emergence orpost-emergence. Specific examples may be mentioned of somerepresentatives of the monocotyledonous and dicotyledonous weed florawhich can be controlled by the compounds according to the invention,without the enumeration being restricted to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous broad-leaved weeds of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens,Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus,Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga,Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia,Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis,Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala,Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus,Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica,Viola, Xanthium.

If the compounds according to the invention are applied to the soilsurface before germination, the weed seedlings are either preventedcompletely from emerging or else the weeds grow until they have reachedthe cotyledon stage, but then their growth stops, and, eventually, afterthree to four weeks have elapsed, they die completely.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth stops after the treatment, and the harmful plantsremain at the growth stage of the point of time of application, or theydie completely after a certain time, so that in this manner competitionby the weeds, which is harmful to the crop plants, is eliminated veryearly and in a sustained manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, ormonocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, in particular Zea and Triticum, are damaged only to aninsignificant extent, or not at all, depending on the structure of therespective compound according to the invention and its application rate.This is why the present compounds are highly suitable for the selectivecontrol of unwanted plant growth in plant crops such as agriculturallyuseful plants or ornamentals.

Moreover, the compounds according to the invention (depending on theirrespective structure and the application rate applied) have outstandinggrowth-regulatory properties in crop plants. They engage in the plant'smetabolism in a regulatory fashion and can therefore be employed for theinfluencing, in a targeted manner, of plant constituents and forfacilitating harvesting, such as, for example, by triggering desiccationand stunted growth. Moreover, they are also suitable for generallycontrolling and inhibiting unwanted vegetative growth without destroyingthe plants in the process. Inhibiting the vegetative growth plays animportant role in many monocotyledonous and dicotyledonous crops sincefor example lodging can be reduced, or prevented completely, hereby.

By virtue of their herbicidal and plant-growth-regulatory properties,the active compounds can also be employed for controlling harmful plantsin crops of genetically modified plants which are known or which are yetto be developed. In general, the transgenic plants are distinguished byespecially advantageous properties, for example by resistances tocertain pesticides, mainly certain herbicides, resistances to plantdiseases or causative organisms of plant diseases, such as certaininsects or microorganisms such as fungi, bacteria or viruses. Otherspecific characteristics relate, for example, to the harvested materialwith regard to quantity, quality, storability, composition and specificconstituents. Thus, transgenic plants are known whose starch content isincreased, or whose starch quality is altered, or those where theharvested material has a different fatty acid composition. Furtherparticular characteristics may lie in tolerance or resistance to abioticstressors, for example, heat, cold, drought, salt, and ultravioletradiation.

It is preferred to use the compounds of the formula (I) according to theinvention or their salts in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet, rice, cassaya and corn or else crops of sugarbeet, cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables.

It is possible with preference to employ the compounds of the formula(I) as herbicides in crops of useful plants which are resistant, or havebeen made resistant by recombinant means, to the phytotoxic effects ofthe herbicides.

Conventional methods of generating novel plants which have modifiedproperties in comparison to plants occurring to date consist, forexample, in traditional breeding methods and the generation of mutants.Alternatively, novel plants with altered properties can be generatedwith the aid of recombinant methods (see, for example, EP 0221044, EP0131624). For example, the following have been described in severalcases:

-   -   the modification, by recombinant technology, of crop plants with        the aim of modifying the starch synthesized in the plants (for        example WO 92/011376 A, WO 92/014827 A, WO 91/019806 A),    -   transgenic crop plants which are resistant to certain herbicides        of the glufosinate type (cf., for example, EP-A-0242236,        EP-A-0242246) or of the glyphosate type (WO 92/000377 A) or of        the sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),        or to combinations or mixtures of these herbicides which are        resistant as a result of ‘gene stacking’, such as transgenic        crop plants, e.g., corn or soybean, with the trade name or with        the designation Optimum™ GAT™ (glyphosate ALS tolerant).    -   transgenic crop plants, for example cotton, with the capability        of producing Bacillus thuringiensis toxins (Bt toxins), which        make the plants resistant to certain pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/013972 A),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 0309862,        EPA0464461),    -   genetically modified plants with reduced photorespiration which        feature higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which are distinguished by higher yields        or better quality,    -   transgenic crop plants which are distinguished by a combination,        for example, of the abovementioned novel properties (“gene        stacking”).

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1(1996) 423-431.

To carry out such recombinant manipulations, nucleic acid moleculeswhich allow mutagenesis or sequence changes by recombination of DNAsequences can be introduced into plasmids. For example, basesubstitutions can be carried out, part-sequences can be removed, ornatural or synthetic sequences may be added with the aid of standardmethods. To link the DNA fragments with one another, it is possible toadd adapters or linkers to the fragments; see, for example, Sambrook etal., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold SpringHarbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Geneand Klone”, VCH Weinheim 2nd ed., 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product.

To this end, it is possible to use DNA molecules which encompass theentire coding sequence of a gene product inclusive of any flankingsequences which may be present, and also DNA molecules which onlyencompass portions of the coding sequence, it being necessary for theseportions to be long enough to have an antisense effect in the cells. Theuse of DNA sequences which have a high degree of homology to the codingsequences of a gene product, but are not completely identical to them,is also possible.

When expressing nucleic acid molecules in plants, the proteinsynthesized can be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to link the coding region with DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants can beplants of any desired plant species, i.e. not only monocotyledonous, butalso dicotyledonous, plants.

Thus, transgenic plants can be obtained whose properties are altered byoverexpression, suppression or inhibition of homologous (=natural) genesor gene sequences or the expression of heterologous (=foreign) genes orgene sequences.

It is preferred to employ the compounds (I) according to the inventionin transgenic crops which are resistant to growth regulators such as,for example, 2,4 D dicamba, or to herbicides which inhibit essentialplant enzymes, for example acetolactate synthases (ALS), EPSP synthases,glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD),or to herbicides from the group of the sulfonylureas, the glyphosates,glufosinates or benzoylisoxazoles and analogous active compounds, or toany combinations of these active compounds.

With particular preference the compounds according to the invention canbe used in transgenic crop plants which are resistant to a combinationof glyphosates and glufosinates, glyphosates and sulfonylureas orimidazolinones. With very particular preference the compounds accordingto the invention can be used in transgenic crop plants such as, forexample, corn or soybean with the tradename or the designation Optimum™GAT™ (glyphosate ALS tolerant).

When the active compounds according to the invention are used intransgenic crops, effects are frequently observed—in addition to theeffects on harmful plants which can be observed in other crops—which arespecific for the application in the transgenic crop in question, forexample a modified or specifically widened spectrum of weeds which canbe controlled, modified application rates which may be employed forapplication, preferably good combinability with the herbicides to whichthe transgenic crop is resistant, and an effect on growth and yield ofthe transgenic crop plants.

The invention therefore also relates to the use of the compounds of theformula (I) according to the invention as herbicides for controllingharmful plants in transgenic crop plants.

The compounds according to the invention can be used in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant growth-regulatingcompositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in variousways according to which biological and/or physicochemical parameters aremandated. Possible formulations include, for example: wettable powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil- or water-based dispersions, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), seed-dressing products,granules for scattering and soil application, granules (GR) in the formof microgranules, spray granules, coated granules and adsorptiongranules, water-dispersible granules (WG), water-soluble granules (SG),ULV formulations, microcapsules and waxes. These individual types offormulation are known in principle and are described, for example, in:Winnacker-Küchler, “Chemische Technologie” [Chemical technology], Volume7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg,“Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “SprayDrying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H.v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxideadducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed.1986.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active compounds, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix. Suitable safeners are, forexample, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl,cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which can be dispersed uniformly inwater and, as well as the active compound, apart from a diluent or inertsubstance, also comprise surfactants of the ionic and/or nonionic type(wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate. Toprepare the wettable powders, the herbicidally active compounds areground finely, for example in customary apparatus such as hammer mills,blower mills and air-jet mills, and simultaneously or subsequently mixedwith the formulation assistants.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents with addition of one ormore surfactants of the ionic and/or nonionic type (emulsifiers). Theemulsifiers used may, for example, be: calcium alkylarylsulfonate saltssuch as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such asfatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan esters, for example sorbitan fatty acidesters, or polyoxyethylene sorbitan esters, for example polyoxyethylenesorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with finelydistributed solid substances, for example talc, natural clays, such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beprepared, for example, by wet grinding by means of commercial bead millsand optional addition of surfactants as have, for example, already beenlisted above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants, as have, forexample, already been listed above for the other formulation types.

Granules can be prepared either by spraying the active compound ontogranular inert material capable of adsorption or by applying activecompound concentrates to the surface of carrier substances, such assand, kaolinites or granular inert material, by means of adhesives, forexample polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitableactive compounds can also be granulated in the manner customary for thepreparation of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are prepared generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the preparation of pan, fluidized bed, extruder and spray granules,see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G.Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical andEngineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”,5th Ed McGraw-Hill, New York 1973, p. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally from 0.1 to 99% byweight, in particular from 0.1 to 95% by weight, of compounds accordingto the invention.

In wettable powders, the active compound concentration is, for example,from about 10 to 90% by weight, the remainder to 100% by weightconsisting of customary formulation components. In the case ofemulsifiable concentrates, the active compound concentration can be fromabout 1 to 90, preferably from 5 to 80, % by weight. Formulations in theform of dusts comprise from 1 to 30% by weight of active compound,preferably usually from 5 to 20% by weight of active compound; sprayablesolutions contain from about 0.05 to 80% by weight, preferably from 2 to50% by weight of active compound. In the case of water-dispersiblegranules, the active compound content depends partially on whether theactive compound is present in liquid or solid form and on whichgranulation auxiliaries, fillers, etc., are used. In thewater-dispersible granules, the content of active compound is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary adhesives, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active compounds, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

Active compounds which can be employed in combination with the compoundsaccording to the invention in mixed formulations or in the tank mix are,for example, known active compounds which are based on the inhibitionof, for example, acetolactate synthase, acetyl-CoA carboxylase,cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutaminesynthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase,photosystem I, photosystem II, protoporphyrinogen oxidase, as aredescribed in, for example, Weed Research 26 (1986) 441-445 or “ThePesticide Manual”, 15th edition, The British Crop Protection Council andthe Royal Soc. of Chemistry, 2003 and the literature cited therein.Known herbicides or plant growth regulators which can be combined withthe compounds according to the invention are, for example, the followingactive compounds (the compounds are either designated by the common nameaccording to the International Organization for Standardization (ISO) orby the chemical name, or by the code number) and always comprise all useforms such as acids, salts, esters and isomers such as stereoisomers andoptical isomers. Here, by way of example, one and in some cases aplurality of use forms are mentioned: acetochlor, acibenzolar,acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen,alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn,amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor,aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam,atrazine, azafenidin, azimsulfuron, aziprotryn, beflubutamid, benazolin,benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide,bensulfuron, bensulfuron-methyl, bentazone, benzfendizone,benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone,bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium,bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos,busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin,butroxydim, butylate, cafenstrole, carbetamide, carfentrazone,carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop,chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac,chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl,chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat chloride,chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron,chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron,clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone,clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl,cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron,cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine,cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet,n-decanol, desmedipham, desmetryn, detosyl pyrazolate (DTP), diallate,dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop,diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl,diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr,diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron,dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid,dipropetryn, diquat, diquat dibromide, dithiopyr, diuron, DNOC,eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin,ethametsulfuron, ethametsulfuron-methyl, ethephon, ethidimuron,ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron,etobenzanid, F-5331, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethanesulfonamide,F-7967, i.e.,3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl,fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate,flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin,flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn,fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,flupoxam, flupropacil, flupropanate, flupyrsulfuron,flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol,flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen,foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid,glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,glyphosate-isopropylammonium, H-9201, i.e.,O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioate,halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P,haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl,haloxyfop-P-methyl, hexazinone, HW-02, i.e.,1-(dimethoxyphosphoryl)-ethyl(2,4-dichlorophenoxy)acetate,imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium,imazapic, imazapyr, imazapyr-isopropylammonium, imazaquin,imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron,inabenfide, indanofan, indaziflam, indoleacetic acid (IAA),4-indol-3-ylbutyric acid (IBA), iodosulfuron,iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone, isocarbamid,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, KUH-043, i.e.,3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole,karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide,MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium,mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium,mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide,mepiquat-chloride, mesosulfuron, mesosulfuron-methyl, mesotrione,methabenzthiazuron, metam, metamifop, metamitron, metazachlor,metazasulfuron, methazole, methiopyrsulfuron, methiozolin,methoxyphenone, methyldymron, 1-methylcyclopropene,methylisothiocyanate, metobenzuron, metobromuron, metolachlor,S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron,metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamidedihydrogensulfate, monolinuron, monosulfuron, monosulfuron-ester,monuron, MT 128, i.e.,6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazin-3-amine,MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide,NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolate sodium(isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paclobutrazol, paraquat,paraquat-dichlorid, pelargonic acid (nonanoic acid), pendimethalin,pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone,pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram,picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl,pretilachlor, primisulfuron, primisulfuron-methyl, probenazole,profluazol, procyazine, prodiamine, prifluraline, profoxydim,prohexadione, prohexadione-calcium, prohydrojasmone, prometon,prometryn, propachlor, propanil, propaquizafop, propazine, propham,propisochlor, propoxycarbazone, propoxycarbazone-sodium,propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron,prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole,pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl,pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl,pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid,pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil,secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, i.e.methyl-(2R)-2({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate,sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron,sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron,SYN-523, SYP-249, i.e.,1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate,SYP-300, i.e.,1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione,tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazafluoron,thiazopyr, thidiazimin, thidiazuron, thiencarbazone,thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl,thiobencarb, tiocarbazil, topramezone, tralkoxydim, triallate,triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl,trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine,trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron,triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl,tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0862i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline,and also the following compounds:

For application, the formulations present in commercial form are, ifappropriate, diluted in a customary manner, for example, in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules, with water. Preparations in the form ofdusts, granules for soil application or granules for broadcasting andsprayable solutions are usually not diluted further with other inertsubstances prior to application.

The required application rate of the compounds of the formula (I) variesaccording to the external conditions such as, inter alia, temperature,humidity and the type of herbicide used. It may vary within wide limits,for example between 0.001 and 1.0 kg/ha or more of active substance;however, preferably it is between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. Chemical Examples

Preparation of5-hydroxy-1,3-dimethyl-4-(2-methyl-3-methylthio-4-pentafluoroethyl-benzoyl)pyrazole(tabular example No. 3-145)

Step 1: Synthesis of 3-fluoro-4-(pentafluoroethyl)bromobenzene

13.2 g (91.9 mmol) of copper(I) bromide were cooled to −5° C. in 80 mlof dry N,N-dimethylformamide. Under nitrogen, 14.7 g (76.7 mmol) oftrimethyl-(pentafluoroethyl)silane were added. 4.45 g (76.7 mmol) ofpotassium fluoride (spray-dried) were added in portions over the courseof 30 minutes at a rate such that the internal temperature remainedbelow 0° C. The mixture was stirred at 0° C. for 1 hour and was thenwarmed to 20° C. over the course of 12 hours. Thereafter 10 ml of dry1,3-dimethyl-2-imidazolidinone and 22 g (73.1 mmol) of3-fluoro-4-iodo-bromobenzene were added. The contents were stirred at75° C. for 14 hours. Then all of the volatile constituents weredistilled off to dryness, the distillate being collected in a cold trapcooled with liquid nitrogen. The distillate was subsequently warmed to20° C. and dissolved in 500 ml of diethyl ether. This solution waswashed with four times 100 ml of water and then with two times 100 ml ofsaturated aqueous NaCl solution. The organic phase was then dried, andthe solvent was removed on a Vigreux column. Subsequent distillation ofthe residue on a Vigreux column gave 16.1 g of product (boiling point:86-87° C. (75 mmHg)) with a purity of 99% by weight.

Step 2: Synthesis of 3-fluoro-4-(pentafluoroethyl)benzoic acid

A solution of 16.0 g (99% by weight; 54.1 mmol) of3-fluoro-4-(pentafluoroethyl)-bromobenzene in 110 ml of THF was cooledto −10° C. Added dropwise over the course of 30 minutes were 36.8 ml ofa 2M (73.6 mmol) solution of isopropyl-magnesium chloride. The mixturewas stirred at −10° C. for 2.5 hours and then cautiously poured onto anexcess of dry ice. For working up, 130 ml of water were added, and themixture was subsequently extracted once with 10 ml of diethyl ether. Theaqueous phase was acidified with half-concentrated hydrochloric acid andthen extracted with four times 150 ml of diethyl ether. The combinedorganic phases were dried and the filtrate was freed from the solvent.The residue was recrystallized from CHCl₃, giving 10.7 g of product witha purity of 98% by weight.

Step 3: Synthesis of 3-fluor-2-methyl-4-(pentafluoroethyl)benzoic acid

5.00 g (98% by weight; 19.0 mmol) of3-fluoro-4-(pentafluoroethyl)benzoic acid were introduced into 40 ml ofdry tetrahydrofuran. 4.73 g (40.7 mmol) of 1,2-bis-(dimethylamino)ethanewere added, and the mixture was then cooled to −40° C. Then 16.3 ml of a2.5 M solution (40.7 mmol) of n-butyllithium in hexane were addeddropwise at a rate such that the temperature was in a range from −33° C.to −35° C. The contents were stirred at −35° C. for 4 hours. Then asolution of 8.25 g (58.1 mmol) of iodomethane in 10 ml of dry THF wasadded dropwise, and the mixture was stirred at −35° C. for 1 hour.Thereafter the contents were warmed to room temperature (RT) and stirredat this temperature for 16 hours. For working up, 50 ml of 2Mhydrochloric acid were cautiously added, and then the aqueous phase wasextracted with diethyl ether. The combined organic phases were dried andfreed from the solvents. The residue was stirred in n-heptane andsubsequently filtered. This gave 2.33 g of residue as a clean product.The filtrate was freed from the solvent, and the residue was againstirred in n-heptane. Filtration produced 590 mg of residue, which wasidentified as a product with a purity of 70% by weight.

Step 4: Synthesis of methyl3-fluoro-2-methyl-4-(pentafluoroethyl)benzoate

2.33 g (8.56 mmol) of 3-fluoro-2-methyl-4-(pentafluoroethyl)benzoic acidwere introduced into 30 ml of methanol and admixed with 2 ml ofconcentrated sulfuric acid. The mixture was subsequently heated atreflux until a check by HPLC indicated full conversion. The contentswere freed from the solvent, and the residue was taken up in water. Themixture was extracted twice with ethyl acetate, and the combined organicphases were washed once with saturated aqueous sodium hydrogen-carbonatesolution. The organic phase was dried and freed from the solvent. Theresidue obtained was 2.1 g of clean product.

Step 5: Synthesis of methyl2-methyl-3-(methylthio)-4-(pentafluoroethyl)benzoate

2.1 g (7.34 mmol) of methyl3-fluoro-2-methyl-4-(pentafluoroethyl)benzoate were introduced into 20ml of N,N-dimethylformamide and then admixed with 758 mg (95% by weight;10.3 mmol) of sodium thiomethoxide. The mixture was stirred at RT for 2hours and then freed from the solvent. The residue was taken up in ethylacetate and water, the aqueous phase was extracted twice with ethylacetate, and, finally, the combined organic phases were dried and freedfrom the solvent. The residue was purified by chromatography, giving1.28 g of clean product.

Step 6: Synthesis of 2-methyl-3-(methylthio)-4-(pentafluoroethyl)benzoicacid

(No. 5-145)

530 mg (1.69 mmol) of methyl2-methyl-3-(methylthio)-4-(pentafluoroethyl)benzoate were introducedinto 10 ml of methanol and admixed with 0.5 ml of 20% strength aqueoussodium hydroxide solution. The contents were stirred at room temperatureuntil a check on the reaction by thin-layer chromatography indicatedcomplete conversion. The mixture was freed from the solvent, and theresidue was taken up in a little water. The mixture was acidified with1M hydrochloric acid, then stirred for 5 minutes and finally filtered.The residue obtained was 470 mg of clean product.

Step 7: Synthesis of1,3-dimethyl-5-(2″-methyl-3″-(methylthio)-4″-(pentafluoroethyl)benzoyloxy)pyrazole

360 mg (1.20 mmol) of2-methyl-3-(methylthio)-4-(pentafluoroethyl)benzoic acid were introducedinto 20 ml of dry dichloromethane and admixed in succession with 198 mg(1.56 mmol) of oxalyl dichloride and also with two drops ofN,N-dimethyl-formamide. After the end of evolution of gas, the mixturewas heated under reflux for 10 minutes. When a check on the reaction bythin-layer chromatography had indicated complete conversion, thecontents were freed from the solvent, and the residue was then taken upin 20 ml of dry dichloromethane. The mixture was admixed with 161 mg(1.44 mmol) of 5-hydroxy-1,3-dimethylpyrazole, and then 243 mg (2.40mmol) of triethylamine were added dropwise. The contents were stirred atRT for 16 hours. For working up, 3 ml of 1M hydrochloric acid wereadded, and, following phase separation, the organic phase was freed fromthe solvent. The residue, finally, was purified by chromatography,giving 410 mg of clean product.

Step 8: Synthesis of5-hydroxy-1,3-dimethyl-4-(2′-methyl-3′-(methylthio)-4′-(pentafluoroethyl)benzoyl)pyrazole(No. 3-145)

136 mg (0.345 mmol) of1,3-dimethyl-5-(2′-methyl-3′-(methylthio)-4′-(pentafluoro-ethyl)benzoyloxy)pyrazolewere introduced into 15 ml of acetonitrile and admixed in successionwith 70 mg (0.69 mmol) of triethylamine and also with eight drops oftrimethylsilyl cyanide. The mixture was stirred at RT for 16 hours. Forworking up, the contents were freed from the solvent, and the residuewas taken up in 15 ml of dichloromethane. 3 ml of 1M hydrochloric acidwere added, and, following phase separation, the organic phase was freedfrom the solvent. The residue was purified by chromatography, giving71.3 mg of product with a purity of 95% by weight.

The examples listed in tables below were prepared in analogy to methodsidentified above or are obtainable in analogy to methods identifiedabove. These compounds are very particularly preferred.

The abbreviations used have the following meanings:

Bu = butyl Et = ethyl Me = methyl Pr = propyl i = iso s = secondary t =tertiary Ph = phenyl

TABLE 1 Inventive compounds of the formula (I) in which R² is methyl,and R³ and R⁴ are each hydrogen

No. X R¹ n Y Physical data: ¹H-NMR: δ [CDCl₃] 1-1 Me Me 0 CF₂Cl 1-2 MeEt 0 CF₂Cl 1-3 Me n-Pr 0 CF₂Cl 1-4 Me i-Pr 0 CF₂Cl 1-5 Me n-Bu 0 CF₂Cl1-6 Me i-Bu 0 CF₂Cl 1-7 Me s-Bu 0 CF₂Cl 1-8 Me t-Bu 0 CF₂Cl 1-9 Me Me 1CF₂Cl 1-10 Me Et 1 CF₂Cl 1-11 Me n-Pr 1 CF₂Cl 1-12 Me i-Pr 1 CF₂Cl 1-13Me n-Bu 1 CF₂Cl 1-14 Me i-Bu 1 CF₂Cl 1-15 Me s-Bu 1 CF₂Cl 1-16 Me t-Bu 1CF₂Cl 1-17 Me Me 2 CF₂Cl 1-18 Me Et 2 CF₂Cl 1-19 Me n-Pr 2 CF₂Cl 1-20 Mei-Pr 2 CF₂Cl 1-21 Me n-Bu 2 CF₂Cl 1-22 Me i-Bu 2 CF₂Cl 1-23 Me s-Bu 2CF₂Cl 1-24 Me t-Bu 2 CF₂Cl 1-25 Et Me 0 CF₂Cl 1-26 Et Et 0 CF₂Cl 1-27 Etn-Pr 0 CF₂Cl 1-28 Et i-Pr 0 CF₂Cl 1-29 Et n-Bu 0 CF₂Cl 1-30 Et i-Bu 0CF₂Cl 1-31 Et s-Bu 0 CF₂Cl 1-32 Et t-Bu 0 CF₂Cl 1-33 Et Me 1 CF₂Cl 1-34Et Et 1 CF₂Cl 1-35 Et n-Pr 1 CF₂Cl 1-36 Et i-Pr 1 CF₂Cl 1-37 Et n-Bu 1CF₂Cl 1-38 Et i-Bu 1 CF₂Cl 1-39 Et s-Bu 1 CF₂Cl 1-40 Et t-Bu 1 CF₂Cl1-41 Et Me 2 CF₂Cl 1-42 Et Et 2 CF₂Cl 1-43 Et n-Pr 2 CF₂Cl 1-44 Et i-Pr2 CF₂Cl 1-45 Et n-Bu 2 CF₂Cl 1-46 Et i-Bu 2 CF₂Cl 1-47 Et s-Bu 2 CF₂Cl1-48 Et t-Bu 2 CF₂Cl 1-49 Me Me 0 CFCl₂ 1-50 Me Et 0 CFCl₂ 1-51 Me n-Pr0 CFCl₂ 1-52 Me i-Pr 0 CFCl₂ 1-53 Me n-Bu 0 CFCl₂ 1-54 Me i-Bu 0 CFCl₂1-55 Me s-Bu 0 CFCl₂ 1-56 Me t-Bu 0 CFCl₂ 1-57 Me Me 1 CFCl₂ 1-58 Me Et1 CFCl₂ 1-59 Me n-Pr 1 CFCl₂ 1-60 Me i-Pr 1 CFCl₂ 1-61 Me n-Bu 1 CFCl₂1-62 Me i-Bu 1 CFCl₂ 1-63 Me s-Bu 1 CFCl₂ 1-64 Me t-Bu 1 CFCl₂ 1-65 MeMe 2 CFCl₂ 1-66 Me Et 2 CFCl₂ 1-67 Me n-Pr 2 CFCl₂ 1-68 Me i-Pr 2 CFCl₂1-69 Me n-Bu 2 CFCl₂ 1-70 Me i-Bu 2 CFCl₂ 1-71 Me s-Bu 2 CFCl₂ 1-72 Met-Bu 2 CFCl₂ 1-73 Et Me 0 CFCl₂ 1-74 Et Et 0 CFCl₂ 1-75 Et n-Pr 0 CFCl₂1-76 Et i-Pr 0 CFCl₂ 1-77 Et n-Bu 0 CFCl₂ 1-78 Et i-Bu 0 CFCl₂ 1-79 Ets-Bu 0 CFCl₂ 1-80 Et t-Bu 0 CFCl₂ 1-81 Et Me 1 CFCl₂ 1-82 Et Et 1 CFCl₂1-83 Et n-Pr 1 CFCl₂ 1-84 Et i-Pr 1 CFCl₂ 1-85 Et n-Bu 1 CFCl₂ 1-86 Eti-Bu 1 CFCl₂ 1-87 Et s-Bu 1 CFCl₂ 1-88 Et t-Bu 1 CFCl₂ 1-89 Et Me 2CFCl₂ 1-90 Et Et 2 CFCl₂ 1-91 Et n-Pr 2 CFCl₂ 1-92 Et i-Pr 2 CFCl₂ 1-93Et n-Bu 2 CFCl₂ 1-94 Et i-Bu 2 CFCl₂ 1-95 Et s-Bu 2 CFCl₂ 1-96 Et t-Bu 2CFCl₂ 1-97 Me Me 0 CCl₃ 1-98 Me Et 0 CCl₃ 1-99 Me n-Pr 0 CCl₃ 1-100 Mei-Pr 0 CCl₃ 1-101 Me n-Bu 0 CCl₃ 1-102 Me i-Bu 0 CCl₃ 1-103 Me s-Bu 0CCl₃ 1-104 Me t-Bu 0 CCl₃ 1-105 Me Me 1 CCl₃ 1-106 Me Et 1 CCl₃ 1-107 Men-Pr 1 CCl₃ 1-108 Me i-Pr 1 CCl₃ 1-109 Me n-Bu 1 CCl₃ 1-110 Me i-Bu 1CCl₃ 1-111 Me s-Bu 1 CCl₃ 1-112 Me t-Bu 1 CCl₃ 1-113 Me Me 2 CCl₃ 1-114Me Et 2 CCl₃ 1-115 Me n-Pr 2 CCl₃ 1-116 Me i-Pr 2 CCl₃ 1-117 Me n-Bu 2CCl₃ 1-118 Me i-Bu 2 CCl₃ 1-119 Me s-Bu 2 CCl₃ 1-120 Me t-Bu 2 CCl₃1-121 Et Me 0 CCl₃ 1-122 Et Et 0 CCl₃ 1-123 Et n-Pr 0 CCl₃ 1-124 Et i-Pr0 CCl₃ 1-125 Et n-Bu 0 CCl₃ 1-126 Et i-Bu 0 CCl₃ 1-127 Et s-Bu 0 CCl₃1-128 Et t-Bu 0 CCl₃ 1-129 Et Me 1 CCl₃ 1-130 Et Et 1 CCl₃ 1-131 Et n-Pr1 CCl₃ 1-132 Et i-Pr 1 CCl₃ 1-133 Et n-Bu 1 CCl₃ 1-134 Et i-Bu 1 CCl₃1-135 Et s-Bu 1 CCl₃ 1-136 Et t-Bu 1 CCl₃ 1-137 Et Me 2 CCl₃ 1-138 Et Et2 CCl₃ 1-139 Et n-Pr 2 CCl₃ 1-140 Et i-Pr 2 CCl₃ 1-141 Et n-Bu 2 CCl₃1-142 Et i-Bu 2 CCl₃ 1-143 Et s-Bu 2 CCl₃ 1-144 Et t-Bu 2 CCl₃ 1-145 MeMe 0 C₂F₅ 7.61 (d, 1H), 7.47 (d, 1H), 7.31 (s, 1H), 3.72 (s, 3H), 2.69(s, 3H), 2.30 (s, 3H) 1-146 Me Et 0 C₂F₅ 1-147 Me n-Pr 0 C₂F₅ 1-148 Mei-Pr 0 C₂F₅ 1-149 Me n-Bu 0 C₂F₅ 1-150 Me i-Bu 0 C₂F₅ 1-151 Me s-Bu 0C₂F₅ 1-152 Me t-Bu 0 C₂F₅ 1-153 Me Me 1 C₂F₅ 7.63 (d, 1H), 7.57 (d, 1H),7.33 (s, 1H), 3.73 (s, 3H), 3.07 (s, 3H), 2.91 (s, 3H) 1-154 Me Et 1C₂F₅ 1-155 Me n-Pr 1 C₂F₅ 1-156 Me i-Pr 1 C₂F₅ 1-157 Me n-Bu 1 C₂F₅1-158 Me i-Bu 1 C₂F₅ 1-159 Me s-Bu 1 C₂F₅ 1-160 Me t-Bu 1 C₂F₅ 1-161 MeMe 2 C₂F₅ 7.76 (d, 1H), 7.64 (d, 1H), 7.30 (s, 1H), 3.73 (s, 3H), 3.29(s, 3H), 2.77 (s, 3H) 1-162 Me Et 2 C₂F₅ 1-163 Me n-Pr 2 C₂F₅ 1-164 Mei-Pr 2 C₂F₅ 1-165 Me n-Bu 2 C₂F₅ 1-166 Me i-Bu 2 C₂F₅ 1-167 Me s-Bu 2C₂F₅ 1-168 Me t-Bu 2 C₂F₅ 1-169 Et Me 0 C₂F₅ 1-170 Et Et 0 C₂F₅ 1-171 Etn-Pr 0 C₂F₅ 1-172 Et i-Pr 0 C₂F₅ 1-173 Et n-Bu 0 C₂F₅ 1-174 Et i-Bu 0C₂F₅ 1-175 Et s-Bu 0 C₂F₅ 1-176 Et t-Bu 0 C₂F₅ 1-177 Et Me 1 C₂F₅ 1-178Et Et 1 C₂F₅ 1-179 Et n-Pr 1 C₂F₅ 1-180 Et i-Pr 1 C₂F₅ 1-181 Et n-Bu 1C₂F₅ 1-182 Et i-Bu 1 C₂F₅ 1-183 Et s-Bu 1 C₂F₅ 1-184 Et t-Bu 1 C₂F₅1-185 Et Me 2 C₂F₅ 1-186 Et Et 2 C₂F₅ 1-187 Et n-Pr 2 C₂F₅ 1-188 Et i-Pr2 C₂F₅ 1-189 Et n-Bu 2 C₂F₅ 1-190 Et i-Bu 2 C₂F₅ 1-191 Et s-Bu 2 C₂F₅1-192 Et t-Bu 2 C₂F₅ 1-193 Me Me 0 CF(CF₃)₂ 1-194 Me Et 0 CF(CF₃)₂ 1-195Me n-Pr 0 CF(CF₃)₂ 1-196 Me i-Pr 0 CF(CF₃)₂ 1-197 Me n-Bu 0 CF(CF₃)₂1-198 Me i-Bu 0 CF(CF₃)₂ 1-199 Me s-Bu 0 CF(CF₃)₂ 1-200 Me t-Bu 0CF(CF₃)₂ 1-201 Me Me 1 CF(CF₃)₂ 1-202 Me Et 1 CF(CF₃)₂ 1-203 Me n-Pr 1CF(CF₃)₂ 1-204 Me i-Pr 1 CF(CF₃)₂ 1-205 Me n-Bu 1 CF(CF₃)₂ 1-206 Me i-Bu1 CF(CF₃)₂ 1-207 Me s-Bu 1 CF(CF₃)₂ 1-208 Me t-Bu 1 CF(CF₃)₂ 1-209 Me Me2 CF(CF₃)₂ 1-210 Me Et 2 CF(CF₃)₂ 1-211 Me n-Pr 2 CF(CF₃)₂ 1-212 Me i-Pr2 CF(CF₃)₂ 1-213 Me n-Bu 2 CF(CF₃)₂ 1-214 Me i-Bu 2 CF(CF₃)₂ 1-215 Mes-Bu 2 CF(CF₃)₂ 1-216 Me t-Bu 2 CF(CF₃)₂ 1-217 Et Me 0 CF(CF₃)₂ 1-218 EtEt 0 CF(CF₃)₂ 1-219 Et n-Pr 0 CF(CF₃)₂ 1-220 Et i-Pr 0 CF(CF₃)₂ 1-221 Etn-Bu 0 CF(CF₃)₂ 1-222 Et i-Bu 0 CF(CF₃)₂ 1-223 Et s-Bu 0 CF(CF₃)₂ 1-224Et t-Bu 0 CF(CF₃)₂ 1-225 Et Me 1 CF(CF₃)₂ 1-226 Et Et 1 CF(CF₃)₂ 1-227Et n-Pr 1 CF(CF₃)₂ 1-228 Et i-Pr 1 CF(CF₃)₂ 1-229 Et n-Bu 1 CF(CF₃)₂1-230 Et i-Bu 1 CF(CF₃)₂ 1-231 Et s-Bu 1 CF(CF₃)₂ 1-232 Et t-Bu 1CF(CF₃)₂ 1-233 Et Me 2 CF(CF₃)₂ 1-234 Et Et 2 CF(CF₃)₂ 1-235 Et n-Pr 2CF(CF₃)₂ 1-236 Et i-Pr 2 CF(CF₃)₂ 1-237 Et n-Bu 2 CF(CF₃)₂ 1-238 Et i-Bu2 CF(CF₃)₂ 1-239 Et s-Bu 2 CF(CF₃)₂ 1-240 Et t-Bu 2 CF(CF₃)₂ 1-241 Me Me0 CHF₂ 1-242 Me Et 0 CHF₂ 1-243 Me n-Pr 0 CHF₂ 1-244 Me i-Pr 0 CHF₂1-245 Me n-Bu 0 CHF₂ 1-246 Me i-Bu 0 CHF₂ 1-247 Me s-Bu 0 CHF₂ 1-248 Met-Bu 0 CHF₂ 1-249 Me Me 1 CHF₂ 1-250 Me Et 1 CHF₂ 1-251 Me n-Pr 1 CHF₂1-252 Me i-Pr 1 CHF₂ 1-253 Me n-Bu 1 CHF₂ 1-254 Me i-Bu 1 CHF₂ 1-255 Mes-Bu 1 CHF₂ 1-256 Me t-Bu 1 CHF₂ 1-257 Me Me 2 CHF₂ 1-258 Me Et 2 CHF₂1-259 Me n-Pr 2 CHF₂ 1-260 Me i-Pr 2 CHF₂ 1-261 Me n-Bu 2 CHF₂ 1-262 Mei-Bu 2 CHF₂ 1-263 Me s-Bu 2 CHF₂ 1-264 Me t-Bu 0 CHF₂ 1-265 Et Me 0 CHF₂1-266 Et Et 0 CHF₂ 1-267 Et n-Pr 0 CHF₂ 1-268 Et i-Pr 0 CHF₂ 1-269 Etn-Bu 0 CHF₂ 1-270 Et i-Bu 0 CHF₂ 1-271 Et s-Bu 0 CHF₂ 1-272 Et t-Bu 0CHF₂ 1-273 Et Me 1 CHF₂ 1-274 Et Et 1 CHF₂ 1-755 Et n-Pr 1 CHF₂ 1-276 Eti-Pr 1 CHF₂ 1-277 Et n-Bu 1 CHF₂ 1-278 Et i-Bu 1 CHF₂ 1-279 Et s-Bu 1CHF₂ 1-280 Et t-Bu 1 CHF₂ 1-281 Et Me 2 CHF₂ 1-282 Et Et 2 CHF₂ 1-283 Etn-Pr 2 CHF₂ 1-284 Et i-Pr 2 CHF₂ 1-285 Et n-Bu 2 CHF₂ 1-286 Et i-Bu 2CHF₂ 1-287 Et s-Bu 2 CHF₂ 1-288 Et t-Bu 2 CHF₂

TABLE 2 Inventive compounds of the formula (I) in which R² is ethyl, andR³ and R⁴ are each hydrogen

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 2-1 Me Me 0 CF₂Cl 2-2 MeEt 0 CF₂Cl 2-3 Me n-Pr 0 CF₂Cl 2-4 Me i-Pr 0 CF₂Cl 2-5 Me n-Bu 0 CF₂Cl2-6 Me i-Bu 0 CF₂Cl 2-7 Me s-Bu 0 CF₂Cl 2-8 Me t-Bu 0 CF₂Cl 2-9 Me Me 1CF₂Cl 2-10 Me Et 1 CF₂Cl 2-11 Me n-Pr 1 CF₂Cl 2-12 Me i-Pr 1 CF₂Cl 2-13Me n-Bu 1 CF₂Cl 2-14 Me i-Bu 1 CF₂Cl 2-15 Me s-Bu 1 CF₂Cl 2-16 Me t-Bu 1CF₂Cl 2-17 Me Me 2 CF₂Cl 2-18 Me Et 2 CF₂Cl 2-19 Me n-Pr 2 CF₂Cl 2-20 Mei-Pr 2 CF₂Cl 2-21 Me n-Bu 2 CF₂Cl 2-22 Me i-Bu 2 CF₂Cl 2-23 Me s-Bu 2CF₂Cl 2-24 Me t-Bu 2 CF₂Cl 2-25 Et Me 0 CF₂Cl 2-26 Et Et 0 CF₂Cl 2-27 Etn-Pr 0 CF₂Cl 2-28 Et i-Pr 0 CF₂Cl 2-29 Et n-Bu 0 CF₂Cl 2-30 Et i-Bu 0CF₂Cl 2-31 Et s-Bu 0 CF₂Cl 2-32 Et t-Bu 0 CF₂Cl 2-33 Et Me 1 CF₂Cl 2-34Et Et 1 CF₂Cl 2-35 Et n-Pr 1 CF₂Cl 2-36 Et i-Pr 1 CF₂Cl 2-37 Et n-Bu 1CF₂Cl 2-38 Et i-Bu 1 CF₂Cl 2-39 Et s-Bu 1 CF₂Cl 2-40 Et t-Bu 1 CF₂Cl2-41 Et Me 2 CF₂Cl 2-42 Et Et 2 CF₂Cl 2-43 Et n-Pr 2 CF₂Cl 2-44 Et i-Pr2 CF₂Cl 2-45 Et n-Bu 2 CF₂Cl 2-46 Et i-Bu 2 CF₂Cl 2-47 Et s-Bu 2 CF₂Cl2-48 Et t-Bu 2 CF₂Cl 2-49 Me Me 0 CFCl₂ 2-50 Me Et 0 CFCl₂ 2-51 Me n-Pr0 CFCl₂ 2-52 Me i-Pr 0 CFCl₂ 2-53 Me n-Bu 0 CFCl₂ 2-54 Me i-Bu 0 CFCl₂2-55 Me s-Bu 0 CFCl₂ 2-56 Me t-Bu 0 CFCl₂ 2-57 Me Me 1 CFCl₂ 2-58 Me Et1 CFCl₂ 2-59 Me n-Pr 1 CFCl₂ 2-60 Me i-Pr 1 CFCl₂ 2-61 Me n-Bu 1 CFCl₂2-62 Me i-Bu 1 CFCl₂ 2-63 Me s-Bu 1 CFCl₂ 2-64 Me t-Bu 1 CFCl₂ 2-65 MeMe 2 CFCl₂ 2-66 Me Et 2 CFCl₂ 2-67 Me n-Pr 2 CFCl₂ 2-68 Me i-Pr 2 CFCl₂2-69 Me n-Bu 2 CFCl₂ 2-70 Me i-Bu 2 CFCl₂ 2-71 Me s-Bu 2 CFCl₂ 2-72 Met-Bu 2 CFCl₂ 2-73 Et Me 0 CFCl₂ 2-74 Et Et 0 CFCl₂ 2-75 Et n-Pr 0 CFCl₂2-76 Et i-Pr 0 CFCl₂ 2-77 Et n-Bu 0 CFCl₂ 2-78 Et i-Bu 0 CFCl₂ 2-79 Ets-Bu 0 CFCl₂ 2-80 Et t-Bu 0 CFCl₂ 2-81 Et Me 1 CFCl₂ 2-82 Et Et 1 CFCl₂2-83 Et n-Pr 1 CFCl₂ 2-84 Et i-Pr 1 CFCl₂ 2-85 Et n-Bu 1 CFCl₂ 2-86 Eti-Bu 1 CFCl₂ 2-87 Et s-Bu 1 CFCl₂ 2-88 Et t-Bu 1 CFCl₂ 2-89 Et Me 2CFCl₂ 2-90 Et Et 2 CFCl₂ 2-91 Et n-Pr 2 CFCl₂ 2-92 Et i-Pr 2 CFCl₂ 2-93Et n-Bu 2 CFCl₂ 2-94 Et i-Bu 2 CFCl₂ 2-95 Et s-Bu 2 CFCl₂ 2-96 Et t-Bu 2CFCl₂ 2-97 Me Me 0 CCl₃ 2-98 Me Et 0 CCl₃ 2-99 Me n-Pr 0 CCl₃ 2-100 Mei-Pr 0 CCl₃ 2-101 Me n-Bu 0 CCl₃ 2-102 Me i-Bu 0 CCl₃ 2-103 Me s-Bu 0CCl₃ 2-104 Me t-Bu 0 CCl₃ 2-105 Me Me 1 CCl₃ 2-106 Me Et 1 CCl₃ 2-107 Men-Pr 1 CCl₃ 2-108 Me i-Pr 1 CCl₃ 2-109 Me n-Bu 1 CCl₃ 2-110 Me i-Bu 1CCl₃ 2-111 Me s-Bu 1 CCl₃ 2-112 Me t-Bu 1 CCl₃ 2-113 Me Me 2 CCl₃ 2-114Me Et 2 CCl₃ 2-115 Me n-Pr 2 CCl₃ 2-116 Me i-Pr 2 CCl₃ 2-117 Me n-Bu 2CCl₃ 2-118 Me i-Bu 2 CCl₃ 2-119 Me s-Bu 2 CCl₃ 2-120 Me t-Bu 2 CCl₃2-121 Et Me 0 CCl₃ 2-122 Et Et 0 CCl₃ 2-123 Et n-Pr 0 CCl₃ 2-124 Et i-Pr0 CCl₃ 2-125 Et n-Bu 0 CCl₃ 2-126 Et i-Bu 0 CCl₃ 2-127 Et s-Bu 0 CCl₃2-128 Et t-Bu 0 CCl₃ 2-129 Et Me 1 CCl₃ 2-130 Et Et 1 CCl₃ 2-131 Et n-Pr1 CCl₃ 2-132 Et i-Pr 1 CCl₃ 2-133 Et n-Bu 1 CCl₃ 2-134 Et i-Bu 1 CCl₃2-135 Et s-Bu 1 CCl₃ 2-136 Et t-Bu 1 CCl₃ 2-137 Et Me 2 CCl₃ 2-138 Et Et2 CCl₃ 2-139 Et n-Pr 2 CCl₃ 2-140 Et i-Pr 2 CCl₃ 2-141 Et n-Bu 2 CCl₃2-142 Et i-Bu 2 CCl₃ 2-143 Et s-Bu 2 CCl₃ 2-144 Et t-Bu 2 CCl₃ 2-145 MeMe 0 C₂F₅ 2-146 Me Et 0 C₂F₅ 2-147 Me n-Pr 0 C₂F₅ 2-148 Me i-Pr 0 C₂F₅2-149 Me n-Bu 0 C₂F₅ 2-150 Me i-Bu 0 C₂F₅ 2-151 Me s-Bu 0 C₂F₅ 2-152 Met-Bu 0 C₂F₅ 2-153 Me Me 1 C₂F₅ 2-154 Me Et 1 C₂F₅ 2-155 Me n-Pr 1 C₂F₅2-156 Me i-Pr 1 C₂F₅ 2-157 Me n-Bu 1 C₂F₅ 2-158 Me i-Bu 1 C₂F₅ 2-159 Mes-Bu 1 C₂F₅ 2-160 Me t-Bu 1 C₂F₅ 2-161 Me Me 2 C₂F₅ 2-162 Me Et 2 C₂F₅2-163 Me n-Pr 2 C₂F₅ 2-164 Me i-Pr 2 C₂F₅ 2-165 Me n-Bu 2 C₂F₅ 2-166 Mei-Bu 2 C₂F₅ 2-167 Me s-Bu 2 C₂F₅ 2-168 Me t-Bu 2 C₂F₅ 2-169 Et Me 0 C₂F₅2-170 Et Et 0 C₂F₅ 2-171 Et n-Pr 0 C₂F₅ 2-172 Et i-Pr 0 C₂F₅ 2-173 Etn-Bu 0 C₂F₅ 2-174 Et i-Bu 0 C₂F₅ 2-175 Et s-Bu 0 C₂F₅ 2-176 Et t-Bu 0C₂F₅ 2-177 Et Me 1 C₂F₅ 2-178 Et Et 1 C₂F₅ 2-179 Et n-Pr 1 C₂F₅ 2-180 Eti-Pr 1 C₂F₅ 2-181 Et n-Bu 1 C₂F₅ 2-182 Et i-Bu 1 C₂F₅ 2-183 Et s-Bu 1C₂F₅ 2-184 Et t-Bu 1 C₂F₅ 2-185 Et Me 2 C₂F₅ 2-186 Et Et 2 C₂F₅ 2-187 Etn-Pr 2 C₂F₅ 2-188 Et i-Pr 2 C₂F₅ 2-189 Et n-Bu 2 C₂F₅ 2-190 Et i-Bu 2C₂F₅ 2-191 Et s-Bu 2 C₂F₅ 2-192 Et t-Bu 2 C₂F₅ 2-193 Me Me 0 CF(CF₃)₂2-194 Me Et 0 CF(CF₃)₂ 2-195 Me n-Pr 0 CF(CF₃)₂ 2-196 Me i-Pr 0 CF(CF₃)₂2-197 Me n-Bu 0 CF(CF₃)₂ 2-198 Me i-Bu 0 CF(CF₃)₂ 2-199 Me s-Bu 0CF(CF₃)₂ 2-200 Me t-Bu 0 CF(CF₃)₂ 2-201 Me Me 1 CF(CF₃)₂ 2-202 Me Et 1CF(CF₃)₂ 2-203 Me n-Pr 1 CF(CF₃)₂ 2-204 Me i-Pr 1 CF(CF₃)₂ 2-205 Me n-Bu1 CF(CF₃)₂ 2-206 Me i-Bu 1 CF(CF₃)₂ 2-207 Me s-Bu 1 CF(CF₃)₂ 2-208 Met-Bu 1 CF(CF₃)₂ 2-209 Me Me 2 CF(CF₃)₂ 2-210 Me Et 2 CF(CF₃)₂ 2-211 Men-Pr 2 CF(CF₃)₂ 2-212 Me i-Pr 2 CF(CF₃)₂ 2-213 Me n-Bu 2 CF(CF₃)₂ 2-214Me i-Bu 2 CF(CF₃)₂ 2-215 Me s-Bu 2 CF(CF₃)₂ 2-216 Me t-Bu 2 CF(CF₃)₂2-217 Et Me 0 CF(CF₃)₂ 2-218 Et Et 0 CF(CF₃)₂ 2-219 Et n-Pr 0 CF(CF₃)₂2-220 Et i-Pr 0 CF(CF₃)₂ 2-221 Et n-Bu 0 CF(CF₃)₂ 2-222 Et i-Bu 0CF(CF₃)₂ 2-223 Et s-Bu 0 CF(CF₃)₂ 2-224 Et t-Bu 0 CF(CF₃)₂ 2-225 Et Me 1CF(CF₃)₂ 2-226 Et Et 1 CF(CF₃)₂ 2-227 Et n-Pr 1 CF(CF₃)₂ 2-228 Et i-Pr 1CF(CF₃)₂ 2-229 Et n-Bu 1 CF(CF₃)₂ 2-230 Et i-Bu 1 CF(CF₃)₂ 2-231 Et s-Bu1 CF(CF₃)₂ 2-232 Et t-Bu 1 CF(CF₃)₂ 2-233 Et Me 2 CF(CF₃)₂ 2-234 Et Et 2CF(CF₃)₂ 2-235 Et n-Pr 2 CF(CF₃)₂ 2-236 Et i-Pr 2 CF(CF₃)₂ 2-237 Et n-Bu2 CF(CF₃)₂ 2-238 Et i-Bu 2 CF(CF₃)₂ 2-239 Et s-Bu 2 CF(CF₃)₂ 2-240 Ett-Bu 2 CF(CF₃)₂ 2-241 Me Me 0 CHF₂ 2-242 Me Et 0 CHF₂ 2-243 Me n-Pr 0CHF₂ 2-244 Me i-Pr 0 CHF₂ 2-245 Me n-Bu 0 CHF₂ 2-246 Me i-Bu 0 CHF₂2-247 Me s-Bu 0 CHF₂ 2-248 Me t-Bu 0 CHF₂ 2-249 Me Me 1 CHF₂ 2-250 Me Et1 CHF₂ 2-251 Me n-Pr 1 CHF₂ 2-252 Me i-Pr 1 CHF₂ 2-253 Me n-Bu 1 CHF₂2-254 Me i-Bu 1 CHF₂ 2-255 Me s-Bu 1 CHF₂ 2-256 Me t-Bu 1 CHF₂ 2-257 MeMe 2 CHF₂ 2-258 Me Et 2 CHF₂ 2-259 Me n-Pr 2 CHF₂ 2-260 Me i-Pr 2 CHF₂2-261 Me n-Bu 2 CHF₂ 2-262 Me i-Bu 2 CHF₂ 2-263 Me s-Bu 2 CHF₂ 2-264 Met-Bu 2 CHF₂ 2-265 Et Me 0 CHF₂ 2-266 Et Et 0 CHF₂ 2-267 Et n-Pr 0 CHF₂2-268 Et i-Pr 0 CHF₂ 2-269 Et n-Bu 0 CHF₂ 2-270 Et i-Bu 0 CHF₂ 2-271 Ets-Bu 0 CHF₂ 2-272 Et t-Bu 0 CHF₂ 2-273 Et Me 1 CHF₂ 2-274 Et Et 1 CHF₂2-275 Et n-Pr 1 CHF₂ 2-276 Et i-Pr 1 CHF₂ 2-277 Et n-Bu 1 CHF₂ 2-278 Eti-Bu 1 CHF₂ 2-279 Et s-Bu 1 CHF₂ 2-280 Et t-Bu 1 CHF₂ 2-281 Et Me 2 CHF₂2-282 Et Et 2 CHF₂ 2-283 Et n-Pr 2 CHF₂ 2-284 Et i-Pr 2 CHF₂ 2-285 Etn-Bu 2 CHF₂ 2-286 Et i-Bu 2 CHF₂ 2-287 Et s-Bu 2 CHF₂ 2-288 Et t-Bu 2CHF₂

TABLE 3 Inventive compounds of the formula (I) in which R² and R³ aremethyl, and R⁴ is hydrogen

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 3-1 Me Me 0 CF₂Cl 3-2 MeEt 0 CF₂Cl 3-3 Me n-Pr 0 CF₂Cl 3-4 Me i-Pr 0 CF₂Cl 3-5 Me n-Bu 0 CF₂Cl3-6 Me i-Bu 0 CF₂Cl 3-7 Me s-Bu 0 CF₂Cl 3-8 Me t-Bu 0 CF₂Cl 3-9 Me Me 1CF₂Cl 3-10 Me Et 1 CF₂Cl 3-11 Me n-Pr 1 CF₂Cl 3-12 Me i-Pr 1 CF₂Cl 3-13Me n-Bu 1 CF₂Cl 3-14 Me i-Bu 1 CF₂Cl 3-15 Me s-Bu 1 CF₂Cl 3-16 Me t-Bu 1CF₂Cl 3-17 Me Me 2 CF₂Cl 3-18 Me Et 2 CF₂Cl 3-19 Me n-Pr 2 CF₂Cl 3-20 Mei-Pr 2 CF₂Cl 3-21 Me n-Bu 2 CF₂Cl 3-22 Me i-Bu 2 CF₂Cl 3-23 Me s-Bu 2CF₂Cl 3-24 Me t-Bu 2 CF₂Cl 3-25 Et Me 0 CF₂Cl 3-26 Et Et 0 CF₂Cl 3-27 Etn-Pr 0 CF₂Cl 3-28 Et i-Pr 0 CF₂Cl 3-29 Et n-Bu 0 CF₂Cl 3-30 Et i-Bu 0CF₂Cl 3-31 Et s-Bu 0 CF₂Cl 3-32 Et t-Bu 0 CF₂Cl 3-33 Et Me 1 CF₂Cl 3-34Et Et 1 CF₂Cl 3-35 Et n-Pr 1 CF₂Cl 3-36 Et i-Pr 1 CF₂Cl 3-37 Et n-Bu 1CF₂Cl 3-38 Et i-Bu 1 CF₂Cl 3-39 Et s-Bu 1 CF₂Cl 3-40 Et t-Bu 1 CF₂Cl3-41 Et Me 2 CF₂Cl 3-42 Et Et 2 CF₂Cl 3-43 Et n-Pr 2 CF₂Cl 3-44 Et i-Pr2 CF₂Cl 3-45 Et n-Bu 2 CF₂Cl 3-46 Et i-Bu 2 CF₂Cl 3-47 Et s-Bu 2 CF₂Cl3-48 Et t-Bu 2 CF₂Cl 3-49 Me Me 0 CFCl₂ 3-50 Me Et 0 CFCl₂ 3-51 Me n-Pr0 CFCl₂ 3-52 Me i-Pr 0 CFCl₂ 3-53 Me n-Bu 0 CFCl₂ 3-54 Me i-Bu 0 CFCl₂3-55 Me s-Bu 0 CFCl₂ 3-56 Me t-Bu 0 CFCl₂ 3-57 Me Me 1 CFCl₂ 3-58 Me Et1 CFCl₂ 3-59 Me n-Pr 1 CFCl₂ 3-60 Me i-Pr 1 CFCl₂ 3-61 Me n-Bu 1 CFCl₂3-62 Me i-Bu 1 CFCl₂ 3-63 Me s-Bu 1 CFCl₂ 3-64 Me t-Bu 1 CFCl₂ 3-65 MeMe 2 CFCl₂ 3-66 Me Et 2 CFCl₂ 3-67 Me n-Pr 2 CFCl₂ 3-68 Me i-Pr 2 CFCl₂3-69 Me n-Bu 2 CFCl₂ 3-70 Me i-Bu 2 CFCl₂ 3-71 Me s-Bu 2 CFCl₂ 3-72 Met-Bu 2 CFCl₂ 3-73 Et Me 0 CFCl₂ 3-74 Et Et 0 CFCl₂ 3-75 Et n-Pr 0 CFCl₂3-76 Et i-Pr 0 CFCl₂ 3-77 Et n-Bu 0 CFCl₂ 3-78 Et i-Bu 0 CFCl₂ 3-79 Ets-Bu 0 CFCl₂ 3-80 Et t-Bu 0 CFCl₂ 3-81 Et Me 1 CFCl₂ 3-82 Et Et 1 CFCl₂3-83 Et n-Pr 1 CFCl₂ 3-84 Et i-Pr 1 CFCl₂ 3-85 Et n-Bu 1 CFCl₂ 3-86 Eti-Bu 1 CFCl₂ 3-87 Et s-Bu 1 CFCl₂ 3-88 Et t-Bu 1 CFCl₂ 3-89 Et Me 2CFCl₂ 3-90 Et Et 2 CFCl₂ 3-91 Et n-Pr 2 CFCl₂ 3-92 Et i-Pr 2 CFCl₂ 3-93Et n-Bu 2 CFCl₂ 3-94 Et i-Bu 2 CFCl₂ 3-95 Et s-Bu 2 CFCl₂ 3-96 Et t-Bu 2CFCl₂ 3-97 Me Me 0 CCl₃ 3-98 Me Et 0 CCl₃ 3-99 Me n-Pr 0 CCl₃ 3-100 Mei-Pr 0 CCl₃ 3-101 Me n-Bu 0 CCl₃ 3-102 Me i-Bu 0 CCl₃ 3-103 Me s-Bu 0CCl₃ 3-104 Me t-Bu 0 CCl₃ 3-105 Me Me 1 CCl₃ 3-106 Me Et 1 CCl₃ 3-107 Men-Pr 1 CCl₃ 3-108 Me i-Pr 1 CCl₃ 3-109 Me n-Bu 1 CCl₃ 3-110 Me i-Bu 1CCl₃ 3-111 Me s-Bu 1 CCl₃ 3-112 Me t-Bu 1 CCl₃ 3-113 Me Me 2 CCl₃ 3-114Me Et 2 CCl₃ 3-115 Me n-Pr 2 CCl₃ 3-116 Me i-Pr 2 CCl₃ 3-117 Me n-Bu 2CCl₃ 3-118 Me i-Bu 2 CCl₃ 3-119 Me s-Bu 2 CCl₃ 3-120 Me t-Bu 2 CCl₃3-121 Et Me 0 CCl₃ 3-122 Et Et 0 CCl₃ 3-123 Et n-Pr 0 CCl₃ 3-124 Et i-Pr0 CCl₃ 3-125 Et n-Bu 0 CCl₃ 3-126 Et i-Bu 0 CCl₃ 3-127 Et s-Bu 0 CCl₃3-128 Et t-Bu 0 CCl₃ 3-129 Et Me 1 CCl₃ 3-130 Et Et 1 CCl₃ 3-131 Et n-Pr1 CCl₃ 3-132 Et i-Pr 1 CCl₃ 3-133 Et n-Bu 1 CCl₃ 3-134 Et i-Bu 1 CCl₃3-135 Et s-Bu 1 CCl₃ 3-136 Et t-Bu 1 CCl₃ 3-137 Et Me 2 CCl₃ 3-138 Et Et2 CCl₃ 3-139 Et n-Pr 2 CCl₃ 3-140 Et i-Pr 2 CCl₃ 3-141 Et n-Bu 2 CCl₃3-142 Et i-Bu 2 CCl₃ 3-143 Et s-Bu 2 CCl₃ 3-144 Et t-Bu 2 CCl₃ 3-145 MeMe 0 C₂F₅ 7.62 (d, 1H), 7.31 (d, 1H), 3.64 (s, 3H), 2.61 (s, 3H), 2.28(s, 3H), 1.63 (s, 3H) 3-146 Me Et 0 C₂F₅ 3-147 Me n-Pr 0 C₂F₅ 3-148 Mei-Pr 0 C₂F₅ 3-149 Me n-Bu 0 C₂F₅ 3-150 Me i-Bu 0 C₂F₅ 3-151 Me s-Bu 0C₂F₅ 3-151 Me t-Bu 0 C₂F₅ 3-153 Me Me 1 C₂F₅ 7.63 (d, 1H), 7.43 (d, 1H),3.66 (s, 3H), 3.03 (s, 3H), 2.86 (s, 3H), 1.67 (s, 3H) 3-154 Me Et 1C₂F₅ 3-155 Me n-Pr 1 C₂F₅ 3-156 Me i-Pr 1 C₂F₅ 3-157 Me n-Bu 1 C₂F₅3-158 Me i-Bu 1 C₂F₅ 3-159 Me s-Bu 1 C₂F₅ 3-160 Me t-Bu 1 C₂F₅ 3-161 MeMe 2 C₂F₅ 7.77 (d, 1H), 7.53 (d, 1H), 3.66 (s, 3H), 3.28 (s, 3H), 2.72(s, 3H), 1.68 (s, 3H) 3-162 Me Et 2 C₂F₅ 3-163 Me n-Pr 2 C₂F₅ 3-164 Mei-Pr 2 C₂F₅ 3-165 Me n-Bu 2 C₂F₅ 3-166 Me i-Bu 2 C₂F₅ 3-167 Me s-Bu 2C₂F₅ 3-168 Me t-Bu 2 C₂F₅ 3-169 Et Me 0 C₂F₅ 3-170 Et Et 0 C₂F₅ 3-171 Etn-Pr 0 C₂F₅ 3-172 Et i-Pr 0 C₂F₅ 3-173 Et n-Bu 0 C₂F₅ 3-174 Et i-Bu 0C₂F₅ 3-175 Et s-Bu 0 C₂F₅ 3-176 Et t-Bu 0 C₂F₅ 3-177 Et Me 1 C₂F₅ 3-178Et Et 1 C₂F₅ 3-179 Et n-Pr 1 C₂F₅ 3-180 Et i-Pr 1 C₂F₅ 3-181 Et n-Bu 1C₂F₅ 3-182 Et i-Bu 1 C₂F₅ 3-183 Et s-Bu 1 C₂F₅ 3-184 Et t-Bu 1 C₂F₅3-185 Et Me 2 C₂F₅ 3-186 Et Et 2 C₂F₅ 3-187 Et n-Pr 2 C₂F₅ 3-188 Et i-Pr2 C₂F₅ 3-189 Et n-Bu 2 C₂F₅ 3-190 Et i-Bu 2 C₂F₅ 3-191 Et s-Bu 2 C₂F₅3-192 Et t-Bu 2 C₂F₅ 3-193 Me Me 0 CF(CF₃)₂ 3-194 Me Et 0 CF(CF₃)₂ 3-195Me n-Pr 0 CF(CF₃)₂ 3-196 Me i-Pr 0 CF(CF₃)₂ 3-197 Me n-Bu 0 CF(CF₃)₂3-198 Me i-Bu 0 CF(CF₃)₂ 3-199 Me s-Bu 0 CF(CF₃)₂ 3-200 Me t-Bu 0CF(CF₃)₂ 3-201 Me Me 1 CF(CF₃)₂ 3-202 Me Et 1 CF(CF₃)₂ 3-203 Me n-Pr 1CF(CF₃)₂ 3-204 Me i-Pr 1 CF(CF₃)₂ 3-205 Me n-Bu 1 CF(CF₃)₂ 3-206 Me i-Bu1 CF(CF₃)₂ 3-207 Me s-Bu 1 CF(CF₃)₂ 3-208 Me t-Bu 1 CF(CF₃)₂ 3-209 Me Me2 CF(CF₃)₂ 3-210 Me Et 2 CF(CF₃)₂ 3-211 Me n-Pr 2 CF(CF₃)₂ 3-212 Me i-Pr2 CF(CF₃)₂ 3-213 Me n-Bu 2 CF(CF₃)₂ 3-214 Me i-Bu 2 CF(CF₃)₂ 3-215 Mes-Bu 2 CF(CF₃)₂ 3-216 Me t-Bu 2 CF(CF₃)₂ 3-217 Et Me 0 CF(CF₃)₂ 3-218 EtEt 0 CF(CF₃)₂ 3-219 Et n-Pr 0 CF(CF₃)₂ 3-220 Et i-Pr 0 CF(CF₃)₂ 3-221 Etn-Bu 0 CF(CF₃)₂ 3-222 Et i-Bu 0 CF(CF₃)₂ 3-223 Et s-Bu 0 CF(CF₃)₂ 3-224Et t-Bu 0 CF(CF₃)₂ 3-225 Et Me 1 CF(CF₃)₂ 3-226 Et Et 1 CF(CF₃)₂ 3-227Et n-Pr 1 CF(CF₃)₂ 3-228 Et i-Pr 1 CF(CF₃)₂ 3-229 Et n-Bu 1 CF(CF₃)₂3-230 Et i-Bu 1 CF(CF₃)₂ 3-231 Et s-Bu 1 CF(CF₃)₂ 3-232 Et t-Bu 1CF(CF₃)₂ 3-233 Et Me 2 CF(CF₃)₂ 3-234 Et Et 2 CF(CF₃)₂ 3-235 Et n-Pr 2CF(CF₃)₂ 3-236 Et i-Pr 2 CF(CF₃)₂ 3-237 Et n-Bu 2 CF(CF₃)₂ 3-238 Et i-Bu2 CF(CF₃)₂ 3-239 Et s-Bu 2 CF(CF₃)₂ 3-240 Et t-Bu 2 CF(CF₃)₂ 3-241 Me Me0 CHF₂ 3-242 Me Et 0 CHF₂ 3-243 Me n-Pr 0 CHF₂ 3-244 Me i-Pr 0 CHF₂3-245 Me n-Bu 0 CHF₂ 3-246 Me i-Bu 0 CHF₂ 3-247 Me s-Bu 0 CHF₂ 3-248 Met-Bu 0 CHF₂ 3-249 Me Me 1 CHF₂ 3-250 Me Et 1 CHF₂ 3-251 Me n-Pr 1 CHF₂3-252 Me i-Pr 1 CHF₂ 3-253 Me n-Bu 1 CHF₂ 3-254 Me i-Bu 1 CHF₂ 3-255 Mes-Bu 1 CHF₂ 3-256 Me t-Bu 1 CHF₂ 3-257 Me Me 2 CHF₂ 3-258 Me Et 2 CHF₂3-259 Me n-Pr 2 CHF₂ 3-260 Me i-Pr 2 CHF₂ 3-261 Me n-Bu 2 CHF₂ 3-262 Mei-Bu 2 CHF₂ 3-263 Me s-Bu 2 CHF₂ 3-264 Me t-Bu 2 CHF₂ 3-265 Et Me 0 CHF₂3-266 Et Et 0 CHF₂ 3-267 Et n-Pr 0 CHF₂ 3-268 Et i-Pr 0 CHF₂ 3-269 Etn-Bu 0 CHF₂ 3-270 Et i-Bu 0 CHF₂ 3-271 Et s-Bu 0 CHF₂ 3-272 Et t-Bu 0CHF₂ 3-273 Et Me 1 CHF₂ 3-274 Et Et 1 CHF₂ 3-275 Et n-Pr 1 CHF₂ 3-276 Eti-Pr 1 CHF₂ 3-277 Et n-Bu 1 CHF₂ 3-278 Et i-Bu 1 CHF₂ 3-279 Et s-Bu 1CHF₂ 3-280 Et t-Bu 1 CHF₂ 3-281 Et Me 2 CHF₂ 3-282 Et Et 2 CHF₂ 3-283 Etn-Pr 2 CHF₂ 3-284 Et i-Pr 2 CHF₂ 3-285 Et n-Bu 2 CHF₂ 3-286 Et i-Bu 2CHF₂ 3-287 Et s-Bu 2 CHF₂ 3-288 Et t-Bu 2 CHF₂

TABLE 4 Inventive compounds of the formula (I)

Physical data: No. R² R³ X R¹ n Y R⁴ ¹H-NMR: δ [CDCl₃] 4-1 Me H Me Me 0CF₂Cl —SO₂-n-Pr 4-2 Me H Me Et 0 CF₂Cl —SO₂-n-Pr 4-3 Me H Me n-Pr 0CF₂Cl —SO₂-n-Pr 4-4 Me H Me Me 1 CF₂Cl —SO₂-n-Pr 4-5 Me H Me Et 1 CF₂Cl—SO₂-n-Pr 4-6 Me H Me n-Pr 1 CF₂Cl —SO₂-n-Pr 4-7 Me H Me Me 2 CF₂Cl—SO₂-n-Pr 4-8 Me H Me Et 2 CF₂Cl —SO₂-n-Pr 4-9 Me H Me n-Pr 2 CF₂Cl—SO₂-n-Pr 4-10 Me H Me Me 0 CF₂Cl —SO₂—(CH₂)₂OMe 4-11 Me H Me Et 0 CF₂Cl—SO₂—(CH₂)₂OMe 4-12 Me H Me n-Pr 0 CF₂Cl —SO₂—(CH₂)₂OMe 4-13 Me H Me Me1 CF₂Cl —SO₂—(CH₂)₂OMe 4-14 Me H Me Et 1 CF₂Cl —SO₂—(CH₂)₂OMe 4-15 Me HMe n-Pr 1 CF₂Cl —SO₂—(CH₂)₂OMe 4-16 Me H Me Me 2 CF₂Cl —SO₂—(CH₂)₂OMe4-17 Me H Me Et 2 CF₂Cl —SO₂—(CH₂)₂OMe 4-18 Me H Me n-Pr 2 CF₂Cl—SO₂—(CH₂)₂OMe 4-19 Me H Me Me 0 CF₂Cl —SO₂—Ph 4-20 Me H Me Et 0 CF₂Cl—SO₂—Ph 4-21 Me H Me n-Pr 0 CF₂Cl —SO₂—Ph 4-22 Me H Me Me 1 CF₂Cl—SO₂—Ph 4-23 Me H Me Et 1 CF₂Cl —SO₂—Ph 4-24 Me H Me n-Pr 1 CF₂Cl—SO₂—Ph 4-25 Me H Me Me 2 CF₂Cl —SO₂—Ph 4-26 Me H Me Et 2 CF₂Cl —SO₂—Ph4-27 Me H Me n-Pr 2 CF₂Cl —SO₂—Ph 4-28 Me H Me Me 0 CF₂Cl —SO₂-(4-Me—Ph)4-29 Me H Me Et 0 CF₂Cl —SO₂-(4-Me—Ph) 4-30 Me H Me n-Pr 0 CF₂Cl—SO₂-(4-Me—Ph) 4-31 Me H Me Me 1 CF₂Cl —SO₂-(4-Me—Ph) 4-32 Me H Me Et 1CF₂Cl —SO₂-—(4-Me—Ph) 4-33 Me H Me n-Pr 1 CF₂Cl —SO₂-(4-Me—Ph) 4-34 Me HMe Me 2 CF₂Cl —SO₂-(4-Me—Ph) 4-35 Me H Me Et 2 CF₂Cl —SO₂-—(4-Me—Ph)4-36 Me H Me n-Pr 2 CF₂Cl —SO₂-—(4-Me—Ph) 4-37 Me H Me Me 0 CF₂Cl—SO₂-(Thien-2-yl) 4-38 Me H Me Et 0 CF₂Cl —SO₂-(Thien-2-yl) 4-39 Me H Men-Pr 0 CF₂Cl —SO₂-(Thien-2-yl) 4-40 Me H Me Me 1 CF₂Cl —SO₂-(Thien-2-yl)4-41 Me H Me Et 1 CF₂Cl —SO₂-(Thien-2-yl) 4-42 Me H Me n-Pr 1 CF₂Cl—SO₂-(Thien-2-yl) 4-43 Me H Me Me 2 CF₂Cl —SO₂-(Thien-2-yl) 4-44 Me H MeEt 2 CF₂Cl —SO₂-(Thien-2-yl) 4-45 Me H Me n-Pr 2 CF₂Cl —SO₂-(Thien-2-yl)4-46 Me H Me Me 0 CF₂Cl —CO—Ph 4-47 Me H Me Et 0 CF₂Cl —CO—Ph 4-48 Me HMe n-Pr 0 CF₂Cl —CO—Ph 4-49 Me H Me Me 1 CF₂Cl —CO—Ph 4-50 Me H Me Et 1CF₂Cl —CO—Ph 4-51 Me H Me n-Pr 1 CF₂Cl —CO—Ph 4-52 Me H Me Me 2 CF₂Cl—CO—Ph 4-53 Me H Me Et 2 CF₂Cl —CO—Ph 4-54 Me H Me n-Pr 2 CF₂Cl —CO—Ph4-55 Me H Me Me 0 CF₂Cl —CH₂—CO—Ph 4-56 Me H Me Et 0 CF₂Cl —CH₂—CO—Ph4-57 Me H Me n-Pr 0 CF₂Cl —CH₂—CO—Ph 4-58 Me H Me Me 1 CF₂Cl —CH₂—CO—Ph4-59 Me H Me Et 1 CF₂Cl —CH₂—CO—Ph 4-60 Me H Me n-Pr 1 CF₂Cl —CH₂—CO—Ph4-61 Me H Me Me 2 CF₂Cl —CH₂—CO—Ph 4-62 Me H Me Et 2 CF₂Cl —CH₂—CO—Ph4-63 Me H Me n-Pr 2 CF₂Cl —CH₂—CO—Ph 4-64 Et H Me Me 0 CF₂Cl —SO₂—n-Pr4-65 Et H Me Et 0 CF₂Cl —SO₂—n-Pr 4-66 Et H Me n-Pr 0 CF₂Cl —SO₂—n-Pr4-67 Et H Me Me 1 CF₂Cl —SO₂—n-Pr 4-68 Et H Me Et 1 CF₂Cl —SO₂—n-Pr 4-69Et H Me n-Pr 1 CF₂Cl —SO₂—n-Pr 4-70 Et H Me Me 2 CF₂Cl —SO₂—n-Pr 4-71 EtH Me Et 2 CF₂Cl —SO₂—n-Pr 4-72 Et H Me n-Pr 2 CF₂Cl —SO₂—n-Pr 4-73 Et HMe Me 0 CF₂Cl —SO₂—(CH₂)₂OMe 4-74 Et H Me Et 0 CF₂Cl —SO₂—(CH₂)₂OMe 4-75Et H Me n-Pr 0 CF₂Cl —SO₂—(CH₂)₂OMe 4-76 Et H Me Me 1 CF₂Cl—SO₂—(CH₂)₂OMe 4-77 Et H Me Et 1 CF₂Cl —SO₂—(CH₂)₂OMe 4-78 Et H Me n-Pr1 CF₂Cl —SO₂—(CH₂)₂OMe 4-79 Et H Me Me 2 CF₂Cl —SO₂—(CH₂)₂OMe 4-80 Et HMe Et 2 CF₂Cl —SO₂—(CH₂)₂OMe 4-81 Et H Me n-Pr 2 CF₂Cl —SO₂—(CH₂)₂OMe4-82 Et H Me Me 0 CF₂Cl —SO₂—Ph 4-83 Et H Me Et 0 CF₂Cl —SO₂—Ph 4-84 EtH Me n-Pr 0 CF₂Cl —SO₂—Ph 4-85 Et H Me Me 1 CF₂Cl —SO₂—Ph 4-86 Et H MeEt 1 CF₂Cl —SO₂—Ph 4-87 Et H Me n-Pr 1 CF₂Cl —SO₂—Ph 4-88 Et H Me Me 2CF₂Cl —SO₂—Ph 4-89 Et H Me Et 2 CF₂Cl —SO₂—Ph 4-90 Et H Me n-Pr 2 CF₂Cl—SO₂—Ph 4-91 Et H Me Me 0 CF₂Cl —SO₂—(4-Me—Ph) 4-92 Et H Me Et 0 CF₂Cl—SO₂—(4-Me—Ph) 4-93 Et H Me n-Pr 0 CF₂Cl —SO₂—(4-Me—Ph) 4-94 Et H Me Me1 CF₂Cl —SO₂—(4-Me—Ph) 4-95 Et H Me Et 1 CF₂Cl —SO₂—(4-Me—Ph) 4-96 Et HMe n-Pr 1 CF₂Cl —SO₂—(4-Me—Ph) 4-97 Et H Me Me 2 CF₂Cl —SO₂—(4-Me—Ph)4-98 Et H Me Et 2 CF₂Cl —SO₂—(4-Me—Ph) 4-99 Et H Me n-Pr 2 CF₂Cl—SO₂—(4-Me—Ph) 4-100 Et H Me Me 0 CF₂Cl —SO₂-(Thien-2-yl) 4-101 Et H MeEt 0 CF₂Cl —SO₂-(Thien-2-yl) 4-102 Et H Me n-Pr 0 CF₂Cl—SO₂-(Thien-2-yl) 4-103 Et H Me Me 1 CF₂Cl —SO₂-(Thien-2-yl) 4-104 Et HMe Et 1 CF₂Cl —SO₂-(Thien-2-yl) 4-105 Et H Me n-Pr 1 CF₂Cl—SO₂-(Thien-2-yl) 4-106 Et H Me Me 2 CF₂Cl —SO₂-(Thien-2-yl) 4-107 Et HMe Et 2 CF₂Cl —SO₂-(Thien-2-yl) 4-108 Et H Me n-Pr 2 CF₂Cl—SO₂-(Thien-2-yl) 4-109 Et H Me Me 0 CF₂Cl —CO—Ph 4-110 Et H Me Et 0CF₂Cl —CO—Ph 4-111 Et H Me n-Pr 0 CF₂Cl —CO—Ph 4-112 Et H Me Me 1 CF₂Cl—CO—Ph 4-113 Et H Me Et 1 CF₂Cl —CO—Ph 4-114 Et H Me n-Pr 1 CF₂Cl —CO—Ph4-115 Et H Me Me 2 CF₂Cl —CO—Ph 4-116 Et H Me Et 2 CF₂Cl —CO—Ph 4-117 EtH Me n-Pr 2 CF₂Cl —CO—Ph 4-118 Et H Me Me 0 CF₂Cl —CH₂—CO—Ph 4-119 Et HMe Et 0 CF₂Cl —CH₂—CO—Ph 4-120 Et H Me n-Pr 0 CF₂Cl —CH₂—CO—Ph 4-121 EtH Me Me 1 CF₂Cl —CH₂—CO—Ph 4-122 Et H Me Et 1 CF₂Cl —CH₂—CO—Ph 4-123 EtH Me n-Pr 1 CF₂Cl —CH₂—CO—Ph 4-124 Et H Me Me 2 CF₂Cl —CH₂—CO—Ph 4-125Et H Me Et 2 CF₂Cl —CH₂—CO—Ph 4-126 Et H Me n-Pr 2 CF₂Cl —CH₂—CO—Ph4-127 Me Me Me Me 0 CF₂Cl —SO₂—n-Pr 4-128 Me Me Me Et 0 CF₂Cl —SO₂—n-Pr4-129 Me Me Me n-Pr 0 CF₂Cl —SO₂—n-Pr 4-130 Me Me Me Me 1 CF₂Cl—SO₂—n-Pr 4-131 Me Me Me Et 1 CF₂Cl —SO₂—n-Pr 4-132 Me Me Me n-Pr 1CF₂Cl —SO₂—n-Pr 4-133 Me Me Me Me 2 CF₂Cl —SO₂—n-Pr 4-134 Me Me Me Et 2CF₂Cl —SO₂—n-Pr 4-135 Me Me Me n-Pr 2 CF₂Cl —SO₂—n-Pr 4-136 Me Me Me Me0 CF₂Cl —SO₂—(CH₂)₂OMe 4-137 Me Me Me Et 0 CF₂Cl —SO₂—(CH₂)₂OMe 4-138 MeMe Me n-Pr 0 CF₂Cl —SO₂—(CH₂)₂OMe 4-139 Me Me Me Me 1 CF₂Cl—SO₂—(CH₂)₂OMe 4-140 Me Me Me Et 1 CF₂Cl —SO₂—(CH₂)₂OMe 4-141 Me Me Men-Pr 1 CF₂Cl —SO₂—(CH₂)₂OMe 4-142 Me Me Me Me 2 CF₂Cl —SO₂—(CH₂)₂OMe4-143 Me Me Me Et 2 CF₂Cl —SO₂—(CH₂)₂OMe 4-144 Me Me Me n-Pr 2 CF₂Cl—SO₂—(CH₂)₂OMe 4-145 Me Me Me Me 0 CF₂Cl —SO₂—Ph 4-146 Me Me Me Et 0CF₂Cl —SO₂—Ph 4-147 Me Me Me n-Pr 0 CF₂Cl —SO₂—Ph 4-148 Me Me Me Me 1CF₂Cl —SO₂—Ph 4-149 Me Me Me Et 1 CF₂Cl —SO₂—Ph 4-150 Me Me Me n-Pr 1CF₂Cl —SO₂—Ph 4-151 Me Me Me Me 2 CF₂Cl —SO₂—Ph 4-152 Me Me Me Et 2CF₂Cl —SO₂—Ph 4-153 Me Me Me n-Pr 2 CF₂Cl —SO₂—Ph 4-154 Me Me Me Me 0CF₂Cl —SO₂—(4-Me—Ph) 4-155 Me Me Me Et 0 CF₂Cl —SO₂—(4-Me—Ph) 4-156 MeMe Me n-Pr 0 CF₂Cl —SO₂—(4-Me—Ph) 4-157 Me Me Me Me 1 CF₂Cl—SO₂—(4-Me—Ph) 4-158 Me Me Me Et 1 CF₂Cl —SO₂—(4-Me—Ph) 4-159 Me Me Men-Pr 1 CF₂Cl —SO₂—(4-Me—Ph) 4-160 Me Me Me Me 2 CF₂Cl —SO₂—(4-Me—Ph)4-161 Me Me Me Et 2 CF₂Cl —SO₂—(4-Me—Ph) 4-162 Me Me Me n-Pr 2 CF₂Cl—SO₂—(4-Me—Ph) 4-163 Me Me Me Me 0 CF₂Cl —SO₂-(Thien-2-yl) 4-164 Me MeMe Et 0 CF₂Cl —SO₂-(Thien-2-yl) 4-165 Me Me Me n-Pr 0 CF₂Cl—SO₂-(Thien-2-yl) 4-166 Me Me Me Me 1 CF₂Cl —SO₂-(Thien-2-yl) 4-167 MeMe Me Et 1 CF₂Cl —SO₂-(Thien-2-yl) 4-168 Me Me Me n-Pr 1 CF₂Cl—SO₂-(Thien-2-yl) 4-169 Me Me Me Me 2 CF₂Cl —SO₂-(Thien-2-yl) 4-170 MeMe Me Et 2 CF₂Cl —SO₂-(Thien-2-yl) 4-171 Me Me Me n-Pr 2 CF₂Cl—SO₂-(Thien-2-yl) 4-172 Me Me Me Me 0 CF₂Cl —CO—Ph 4-173 Me Me Me Et 0CF₂Cl —CO—Ph 4-174 Me Me Me n-Pr 0 CF₂Cl —CO—Ph 4-175 Me Me Me Me 1CF₂Cl —CO—Ph 4-176 Me Me Me Et 1 CF₂Cl —CO—Ph 4-177 Me Me Me n-Pr 1CF₂Cl —CO—Ph 4-178 Me Me Me Me 2 CF₂Cl —CO—Ph 4-179 Me Me Me Et 2 CF₂Cl—CO—Ph 4-180 Me Me Me n-Pr 2 CF₂Cl —CO—Ph 4-181 Me Me Me Me 0 CF₂Cl—CH₂—CO—Ph 4-182 Me Me Me Et 0 CF₂Cl —CH₂—CO—Ph 4-183 Me Me Me n-Pr 0CF₂Cl —CH₂—CO—Ph 4-184 Me Me Me Me 1 CF₂Cl —CH₂—CO—Ph 4-185 Me Me Me Et1 CF₂Cl —CH₂—CO—Ph 4-186 Me Me Me n-Pr 1 CF₂Cl —CH₂—CO—Ph 4-187 Me Me MeMe 2 CF₂Cl —CH₂—CO—Ph 4-188 Me Me Me Et 2 CF₂Cl —CH₂—CO—Ph 4-189 Me MeMe n-Pr 2 CF₂Cl —CH₂—CO—Ph 4-190 Me H Me Me 0 CFCl₂ —SO₂—n-Pr 4-191 Me HMe Et 0 CFCl₂ —SO₂—n-Pr 4-192 Me H Me n-Pr 0 CFCl₂ —SO₂—n-Pr 4-193 Me HMe Me 1 CFCl₂ —SO₂—n-Pr 4-194 Me H Me Et 1 CFCl₂ —SO₂—n-Pr 4-195 Me H Men-Pr 1 CFCl₂ —SO₂—n-Pr 4-196 Me H Me Me 2 CFCl₂ —SO₂—n-Pr 4-197 Me H MeEt 2 CFCl₂ —SO₂—n-Pr 4-198 Me H Me n-Pr 2 CFCl₂ —SO₂—n-Pr 4-199 Me H MeMe 0 CFCl₂ —SO₂—(CH₂)₂OMe 4-200 Me H Me Et 0 CFCl₂ —SO₂—(CH₂)₂OMe 4-201Me H Me n-Pr 0 CFCl₂ —SO₂—(CH₂)₂OMe 4-202 Me H Me Me 1 CFCl₂—SO₂—(CH₂)₂OMe 4-203 Me H Me Et 1 CFCl₂ —SO₂—(CH₂)₂OMe 4-204 Me H Men-Pr 1 CFCl₂ —SO₂—(CH₂)₂OMe 4-205 Me H Me Me 2 CFCl₂ —SO₂—(CH₂)₂OMe4-206 Me H Me Et 2 CFCl₂ —SO₂—(CH₂)₂OMe 4-207 Me H Me n-Pr 2 CFCl₂—SO₂—(CH₂)₂OMe 4-208 Me H Me Me 0 CFCl₂ —SO₂—Ph 4-209 Me H Me Et 0 CFCl₂—SO₂—Ph 4-210 Me H Me n-Pr 0 CFCl₂ —SO₂—Ph 4-211 Me H Me Me 1 CFCl₂—SO₂—Ph 4-212 Me H Me Et 1 CFCl₂ —SO₂—Ph 4-213 Me H Me n-Pr 1 CFCl₂—SO₂—Ph 4-214 Me H Me Me 2 CFCl₂ —SO₂—Ph 4-215 Me H Me Et 2 CFCl₂—SO₂—Ph 4-216 Me H Me n-Pr 2 CFCl₂ —SO₂—Ph 4-217 Me H Me Me 0 CFCl₂—SO₂—(4-Me—Ph) 4-218 Me H Me Et 0 CFCl₂ —SO₂—(4-Me—Ph) 4-219 Me H Men-Pr 0 CFCl₂ —SO₂—(4-Me—Ph) 4-220 Me H Me Me 1 CFCl₂ —SO₂—(4-Me—Ph)4-221 Me H Me Et 1 CFCl₂ —SO₂—(4-Me—Ph) 4-222 Me H Me n-Pr 1 CFCl₂—SO₂—(4-Me—Ph) 4-223 Me H Me Me 2 CFCl₂ —SO₂—(4-Me—Ph) 4-224 Me H Me Et2 CFCl₂ —SO₂—(4-Me—Ph) 4-225 Me H Me n-Pr 2 CFCl₂ —SO₂—(4-Me—Ph) 4-226Me H Me Me 0 CFCl₂ —SO₂-(Thien-2-yl) 4-227 Me H Me Et 0 CFCl₂—SO₂-(Thien-2-yl) 4-228 Me H Me n-Pr 0 CFCl₂ —SO₂-(Thien-2-yl) 4-229 MeH Me Me 1 CFCl₂ —SO₂-(Thien-2-yl) 4-230 Me H Me Et 1 CFCl₂—SO₂-(Thien-2-yl) 4-231 Me H Me n-Pr 1 CFCl₂ —SO₂-(Thien-2-yl) 4-232 MeH Me Me 2 CFCl₂ —SO₂-(Thien-2-yl) 4-233 Me H Me Et 2 CFCl₂—SO₂-(Thien-2-yl) 4-234 Me H Me n-Pr 2 CFCl₂ —SO₂-(Thien-2-yl) 4-235 MeH Me Me 0 CFCl₂ —CO—Ph 4-236 Me H Me Et 0 CFCl₂ —CO—Ph 4-237 Me H Men-Pr 0 CFCl₂ —CO—Ph 4-238 Me H Me Me 1 CFCl₂ —CO—Ph 4-239 Me H Me Et 1CFCl₂ —CO—Ph 4-240 Me H Me n-Pr 1 CFCl₂ —CO—Ph 4-241 Me H Me Me 2 CFCl₂—CO—Ph 4-242 Me H Me Et 2 CFCl₂ —CO—Ph 4-243 Me H Me n-Pr 2 CFCl₂ —CO—Ph4-244 Me H Me Me 0 CFCl₂ —CH₂—CO—Ph 4-245 Me H Me Et 0 CFCl₂ —CH₂—CO—Ph4-246 Me H Me n-Pr 0 CFCl₂ —CH₂—CO—Ph 4-247 Me H Me Me 1 CFCl₂—CH₂—CO—Ph 4-248 Me H Me Et 1 CFCl₂ —CH₂—CO—Ph 4-249 Me H Me n-Pr 1CFCl₂ —CH₂—CO—Ph 4-250 Me H Me Me 2 CFCl₂ —CH₂—CO—Ph 4-251 Me H Me Et 2CFCl₂ —CH₂—CO—Ph 4-252 Me H Me n-Pr 2 CFCl₂ —CH₂—CO—Ph 4-253 Et H Me Me0 CFCl₂ —SO₂—n-Pr 4-254 Et H Me Et 0 CFCl₂ —SO₂—n-Pr 4-255 Et H Me n-Pr0 CFCl₂ —SO₂—n-Pr 4-256 Et H Me Me 1 CFCl₂ —SO₂—n-Pr 4-257 Et H Me Et 1CFCl₂ —SO₂—n-Pr 4-258 Et H Me n-Pr 1 CFCl₂ —SO₂—n-Pr 4-259 Et H Me Me 2CFCl₂ —SO₂—n-Pr 4-260 Et H Me Et 2 CFCl₂ —SO₂—n-Pr 4-261 Et H Me n-Pr 2CFCl₂ —SO₂—n-Pr 4-262 Et H Me Me 0 CFCl₂ —SO₂—(CH₂)₂OMe 4-263 Et H Me Et0 CFCl₂ —SO₂—(CH₂)₂OMe 4-264 Et H Me n-Pr 0 CFCl₂ —SO₂—(CH₂)₂OMe 4-265Et H Me Me 1 CFCl₂ —SO₂—(CH₂)₂OMe 4-266 Et H Me Et 1 CFCl₂—SO₂—(CH₂)₂OMe 4-267 Et H Me n-Pr 1 CFCl₂ —SO₂—(CH₂)₂OMe 4-268 Et H MeMe 2 CFCl₂ —SO₂—(CH₂)₂OMe 4-269 Et H Me Et 2 CFCl₂ —SO₂—(CH₂)₂OMe 4-270Et H Me n-Pr 2 CFCl₂ —SO₂—(CH₂)₂OMe 4-271 Et H Me Me 0 CFCl₂ —SO₂—Ph4-272 Et H Me Et 0 CFCl₂ —SO₂—Ph 4-273 Et H Me n-Pr 0 CFCl₂ —SO₂—Ph4-274 Et H Me Me 1 CFCl₂ —SO₂—Ph 4-275 Et H Me Et 1 CFCl₂ —SO₂—Ph 4-276Et H Me n-Pr 1 CFCl₂ —SO₂—Ph 4-277 Et H Me Me 2 CFCl₂ —SO₂—Ph 4-278 Et HMe Et 2 CFCl₂ —SO₂—Ph 4-279 Et H Me n-Pr 2 CFCl₂ —SO₂—Ph 4-280 Et H MeMe 0 CFCl₂ —SO₂—(4-Me—Ph) 4-281 Et H Me Et 0 CFCl₂ —SO₂—(4-Me—Ph) 4-282Et H Me n-Pr 0 CFCl₂ —SO₂—(4-Me—Ph) 4-283 Et H Me Me 1 CFCl₂—SO₂—(4-Me—Ph) 4-284 Et H Me Et 1 CFCl₂ —SO₂—(4-Me—Ph) 4-285 Et H Men-Pr 1 CFCl₂ —SO₂—(4-Me—Ph) 4-286 Et H Me Me 2 CFCl₂ —SO₂—(4-Me—Ph)4-287 Et H Me Et 2 CFCl₂ —SO₂—(4-Me—Ph) 4-288 Et H Me n-Pr 2 CFCl₂—SO₂—(4-Me—Ph) 4-289 Et H Me Me 0 CFCl₂ —SO₂-(Thien-2-yl) 4-290 Et H MeEt 0 CFCl₂ —SO₂-(Thien-2-yl) 4-291 Et H Me n-Pr 0 CFCl₂—SO₂-(Thien-2-yl) 4-292 Et H Me Me 1 CFCl₂ —SO₂-(Thien-2-yl) 4-293 Et HMe Et 1 CFCl₂ —SO₂-(Thien-2-yl) 4-294 Et H Me n-Pr 1 CFCl₂—SO₂-(Thien-2-yl) 4-295 Et H Me Me 2 CFCl₂ —SO₂-(Thien-2-yl) 4-296 Et HMe Et 2 CFCl₂ —SO₂-(Thien-2-yl) 4-297 Et H Me n-Pr 2 CFCl₂—SO₂-(Thien-2-yl) 4-298 Et H Me Me 0 CFCl₂ —CO—Ph 4-299 Et H Me Et 0CFCl₂ —CO—Ph 4-300 Et H Me n-Pr 0 CFCl₂ —CO—Ph 4-301 Et H Me Me 1 CFCl₂—CO—Ph 4-302 Et H Me Et 1 CFCl₂ —CO—Ph 4-303 Et H Me n-Pr 1 CFCl₂ —CO—Ph4-304 Et H Me Me 2 CFCl₂ —CO—Ph 4-305 Et H Me Et 2 CFCl₂ —CO—Ph 4-306 EtH Me n-Pr 2 CFCl₂ —CO—Ph 4-307 Et H Me Me 0 CFCl₂ —CH₂—CO—Ph 4-308 Et HMe Et 0 CFCl₂ —CH₂—CO—Ph 4-309 Et H Me n-Pr 0 CFCl₂ —CH₂—CO—Ph 4-310 EtH Me Me 1 CFCl₂ —CH₂—CO—Ph 4-311 Et H Me Et 1 CFCl₂ —CH₂—CO—Ph 4-312 EtH Me n-Pr 1 CFCl₂ —CH₂—CO—Ph 4-313 Et H Me Me 2 CFCl₂ —CH₂—CO—Ph 4-314Et H Me Et 2 CFCl₂ —CH₂—CO—Ph 4-315 Et H Me n-Pr 2 CFCl₂ —CH₂—CO—Ph4-316 Me Me Me Me 0 CFCl₂ —SO₂—n-Pr 4-317 Me Me Me Et 0 CFCl₂ —SO₂—n-Pr4-318 Me Me Me n-Pr 0 CFCl₂ —SO₂—n-Pr 4-319 Me Me Me Me 1 CFCl₂—SO₂—n-Pr 4-320 Me Me Me Et 1 CFCl₂ —SO₂—n-Pr 4-321 Me Me Me n-Pr 1CFCl₂ —SO₂—n-Pr 4-322 Me Me Me Me 2 CFCl₂ —SO₂—n-Pr 4-323 Me Me Me Et 2CFCl₂ —SO₂—n-Pr 4-324 Me Me Me n-Pr 2 CFCl₂ —SO₂—n-Pr 4-325 Me Me Me Me0 CFCl₂ —SO₂—(CH₂)₂OMe 4-326 Me Me Me Et 0 CFCl₂ —SO₂—(CH₂)₂OMe 4-327 MeMe Me n-Pr 0 CFCl₂ —SO₂—(CH₂)₂OMe 4-328 Me Me Me Me 1 CFCl₂—SO₂—(CH₂)₂OMe 4-329 Me Me Me Et 1 CFCl₂ —SO₂—(CH₂)₂OMe 4-330 Me Me Men-Pr 1 CFCl₂ —SO₂—(CH₂)₂OMe 4-331 Me Me Me Me 2 CFCl₂ —SO₂—(CH₂)₂OMe4-332 Me Me Me Et 2 CFCl₂ —SO₂—(CH₂)₂OMe 4-333 Me Me Me n-Pr 2 CFCl₂—SO₂—(CH₂)₂OMe 4-334 Me Me Me Me 0 CFCl₂ —SO₂—Ph 4-335 Me Me Me Et 0CFCl₂ —SO₂—Ph 4-336 Me Me Me n-Pr 0 CFCl₂ —SO₂—Ph 4-337 Me Me Me Me 1CFCl₂ —SO₂—Ph 4-338 Me Me Me Et 1 CFCl₂ —SO₂—Ph 4-339 Me Me Me n-Pr 1CFCl₂ —SO₂—Ph 4-340 Me Me Me Me 2 CFCl₂ —SO₂—Ph 4-341 Me Me Me Et 2CFCl₂ —SO₂—Ph 4-342 Me Me Me n-Pr 2 CFCl₂ —SO₂—Ph 4-343 Me Me Me Me 0CFCl₂ —SO₂—(4-Me—Ph) 4-344 Me Me Me Et 0 CFCl₂ —SO₂—(4-Me—Ph) 4-345 MeMe Me n-Pr 0 CFCl₂ —SO₂—(4-Me—Ph) 4-346 Me Me Me Me 1 CFCl₂—SO₂—(4-Me—Ph) 4-347 Me Me Me Et 1 CFCl₂ —SO₂—(4-Me—Ph) 4-348 Me Me Men-Pr 1 CFCl₂ —SO₂—(4-Me—Ph) 4-349 Me Me Me Me 2 CFCl₂ —SO₂—(4-Me—Ph)4-350 Me Me Me Et 2 CFCl₂ —SO₂—(4-Me—Ph) 4-351 Me Me Me n-Pr 2 CFCl₂—SO₂—(4-Me—Ph) 4-352 Me Me Me Me 0 CFCl₂ —SO₂-(Thien-2-yl) 4-353 Me MeMe Et 0 CFCl₂ —SO₂-(Thien-2-yl) 4-354 Me Me Me n-Pr 0 CFCl₂—SO₂-(Thien-2-yl) 4-355 Me Me Me Me 1 CFCl₂ —SO₂-(Thien-2-yl) 4-356 MeMe Me Et 1 CFCl₂ —SO₂-(Thien-2-yl) 4-357 Me Me Me n-Pr 1 CFCl₂—SO₂-(Thien-2-yl) 4-358 Me Me Me Me 2 CFCl₂ —SO₂-(Thien-2-yl) 4-359 MeMe Me Et 2 CFCl₂ —SO₂-(Thien-2-yl) 4-360 Me Me Me n-Pr 2 CFCl₂—SO₂-(Thien-2-yl) 4-361 Me Me Me Me 0 CFCl₂ —CO—Ph 4-362 Me Me Me Et 0CFCl₂ —CO—Ph 4-363 Me Me Me n-Pr 0 CFCl₂ —CO—Ph 4-364 Me Me Me Me 1CFCl₂ —CO—Ph 4-365 Me Me Me Et 1 CFCl₂ —CO—Ph 4-366 Me Me Me n-Pr 1CFCl₂ —CO—Ph 4-367 Me Me Me Me 2 CFCl₂ —CO—Ph 4-368 Me Me Me Et 2 CFCl₂—CO—Ph 4-369 Me Me Me n-Pr 2 CFCl₂ —CO—Ph 4-370 Me Me Me Me 0 CFCl₂—CH₂—CO—Ph 4-371 Me Me Me Et 0 CFCl₂ —CH₂—CO—Ph 4-372 Me Me Me n-Pr 0CFCl₂ —CH₂—CO—Ph 4-373 Me Me Me Me 1 CFCl₂ —CH₂—CO—Ph 4-374 Me Me Me Et1 CFCl₂ —CH₂—CO—Ph 4-375 Me Me Me n-Pr 1 CFCl₂ —CH₂—CO—Ph 4-376 Me Me MeMe 2 CFCl₂ —CH₂—CO—Ph 4-377 Me Me Me Et 2 CFCl₂ —CH₂—CO—Ph 4-378 Me MeMe n-Pr 2 CFCl₂ —CH₂—CO—Ph 4-379 Me H Me Me 0 CCl₃ —SO₂—n-Pr 4-380 Me HMe Et 0 CCl₃ —SO₂—n-Pr 4-381 Me H Me n-Pr 0 CCl₃ —SO₂—n-Pr 4-382 Me H MeMe 1 CCl₃ —SO₂—n-Pr 4-383 Me H Me Et 1 CCl₃ —SO₂—n-Pr 4-384 Me H Me n-Pr1 CCl₃ —SO₂—n-Pr 4-385 Me H Me Me 2 CCl₃ —SO₂—n-Pr 4-386 Me H Me Et 2CCl₃ —SO₂—n-Pr 4-387 Me H Me n-Pr 2 CCl₃ —SO₂—n-Pr 4-388 Me H Me Me 0CCl₃ —SO₂—(CH₂)₂OMe 4-389 Me H Me Et 0 CCl₃ —SO₂—(CH₂)₂OMe 4-390 Me H Men-Pr 0 CCl₃ —SO₂—(CH₂)₂OMe 4-391 Me H Me Me 1 CCl₃ —SO₂—(CH₂)₂OMe 4-392Me H Me Et 1 CCl₃ —SO₂—(CH₂)₂OMe 4-393 Me H Me n-Pr 1 CCl₃—SO₂—(CH₂)₂OMe 4-394 Me H Me Me 2 CCl₃ —SO₂—(CH₂)₂OMe 4-395 Me H Me Et 2CCl₃ —SO₂—(CH₂)₂OMe 4-396 Me H Me n-Pr 2 CCl₃ —SO₂—(CH₂)₂OMe 4-397 Me HMe Me 0 CCl₃ —SO₂—Ph 4-398 Me H Me Et 0 CCl₃ —SO₂—Ph 4-399 Me H Me n-Pr0 CCl₃ —SO₂—Ph 4-400 Me H Me Me 1 CCl₃ —SO₂—Ph 4-401 Me H Me Et 1 CCl₃—SO₂—Ph 4-402 Me H Me n-Pr 1 CCl₃ —SO₂—Ph 4-403 Me H Me Me 2 CCl₃—SO₂—Ph 4-404 Me H Me Et 2 CCl₃ —SO₂—Ph 4-405 Me H Me n-Pr 2 CCl₃—SO₂—Ph 4-406 Me H Me Me 0 CCl₃ —SO₂—(4-Me—Ph) 4-407 Me H Me Et 0 CCl₃—SO₂—(4-Me—Ph) 4-408 Me H Me n-Pr 0 CCl₃ —SO₂—(4-Me—Ph) 4-409 Me H Me Me1 CCl₃ —SO₂—(4-Me—Ph) 4-410 Me H Me Et 1 CCl₃ —SO₂—(4-Me—Ph) 4-411 Me HMe n-Pr 1 CCl₃ —SO₂—(4-Me—Ph) 4-412 Me H Me Me 2 CCl₃ —SO₂—(4-Me—Ph)4-413 Me H Me Et 2 CCl₃ —SO₂—(4-Me—Ph) 4-414 Me H Me n-Pr 2 CCl₃—SO₂—(4-Me—Ph) 4-415 Me H Me Me 0 CCl₃ —SO₂-(Thien-2-yl) 4-416 Me H MeEt 0 CCl₃ —SO₂-(Thien-2-yl) 4-417 Me H Me n-Pr 0 CCl₃ —SO₂-(Thien-2-yl)4-418 Me H Me Me 1 CCl₃ —SO₂-(Thien-2-yl) 4-419 Me H Me Et 1 CCl₃—SO₂-(Thien-2-yl) 4-420 Me H Me n-Pr 1 CCl₃ —SO₂-(Thien-2-yl) 4-421 Me HMe Me 2 CCl₃ —SO₂-(Thien-2-yl) 4-422 Me H Me Et 2 CCl₃ —SO₂-(Thien-2-yl)4-423 Me H Me n-Pr 2 CCl₃ —SO₂-(Thien-2-yl) 4-424 Me H Me Me 0 CCl₃—CO—Ph 4-425 Me H Me Et 0 CCl₃ —CO—Ph 4-426 Me H Me n-Pr 0 CCl₃ —CO—Ph4-427 Me H Me Me 1 CCl₃ —CO—Ph 4-428 Me H Me Et 1 CCl₃ —CO—Ph 4-429 Me HMe n-Pr 1 CCl₃ —CO—Ph 4-430 Me H Me Me 2 CCl₃ —CO—Ph 4-431 Me H Me Et 2CCl₃ —CO—Ph 4-432 Me H Me n-Pr 2 CCl₃ —CO—Ph 4-433 Me H Me Me 0 CCl₃—CH₂—CO—Ph 4-434 Me H Me Et 0 CCl₃ —CH₂—CO—Ph 4-435 Me H Me n-Pr 0 CCl₃—CH₂—CO—Ph 4-436 Me H Me Me 1 CCl₃ —CH₂—CO—Ph 4-437 Me H Me Et 1 CCl₃—CH₂—CO—Ph 4-438 Me H Me n-Pr 1 CCl₃ —CH₂—CO—Ph 4-439 Me H Me Me 2 CCl₃—CH₂—CO—Ph 4-440 Me H Me Et 2 CCl₃ —CH₂—CO—Ph 4-441 Me H Me n-Pr 2 CCl₃—CH₂—CO—Ph 4-442 Et H Me Me 0 CCl₃ —SO₂—n-Pr 4-443 Et H Me Et 0 CCl₃—SO₂—n-Pr 4-444 Et H Me n-Pr 0 CCl₃ —SO₂—n-Pr 4-445 Et H Me Me 1 CCl₃—SO₂—n-Pr 4-446 Et H Me Et 1 CCl₃ —SO₂—n-Pr 4-447 Et H Me n-Pr 1 CCl₃—SO₂—n-Pr 4-448 Et H Me Me 2 CCl₃ —SO₂—n-Pr 4-449 Et H Me Et 2 CCl₃—SO₂—n-Pr 4-450 Et H Me n-Pr 2 CCl₃ —SO₂—n-Pr 4-451 Et H Me Me 0 CCl₃—SO₂—(CH₂)₂OMe 4-452 Et H Me Et 0 CCl₃ —SO₂—(CH₂)₂OMe 4-453 Et H Me n-Pr0 CCl₃ —SO₂—(CH₂)₂OMe 4-454 Et H Me Me 1 CCl₃ —SO₂—(CH₂)₂OMe 4-455 Et HMe Et 1 CCl₃ —SO₂—(CH₂)₂OMe 4-456 Et H Me n-Pr 1 CCl₃ —SO₂—(CH₂)₂OMe4-457 Et H Me Me 2 CCl₃ —SO₂—(CH₂)₂OMe 4-458 Et H Me Et 2 CCl₃—SO₂—(CH₂)₂OMe 4-459 Et H Me n-Pr 2 CCl₃ —SO₂—(CH₂)₂OMe 4-460 Et H Me Me0 CCl₃ —SO₂—Ph 4-461 Et H Me Et 0 CCl₃ —SO₂—Ph 4-462 Et H Me n-Pr 0 CCl₃—SO₂—Ph 4-463 Et H Me Me 1 CCl₃ —SO₂—Ph 4-464 Et H Me Et 1 CCl₃ —SO₂—Ph4-465 Et H Me n-Pr 1 CCl₃ —SO₂—Ph 4-466 Et H Me Me 2 CCl₃ —SO₂—Ph 4-467Et H Me Et 2 CCl₃ —SO₂—Ph 4-468 Et H Me n-Pr 2 CCl₃ —SO₂—Ph 4-469 Et HMe Me 0 CCl₃ —SO₂—(4-Me—Ph) 4-470 Et H Me Et 0 CCl₃ —SO₂—(4-Me—Ph) 4-471Et H Me n-Pr 0 CCl₃ —SO₂—(4-Me—Ph) 4-472 Et H Me Me 1 CCl₃—SO₂—(4-Me—Ph) 4-473 Et H Me Et 1 CCl₃ —SO₂—(4-Me—Ph) 4-474 Et H Me n-Pr1 CCl₃ —SO₂—(4-Me—Ph) 4-475 Et H Me Me 2 CCl₃ —SO₂—(4-Me—Ph) 4-476 Et HMe Et 2 CCl₃ —SO₂—(4-Me—Ph) 4-477 Et H Me n-Pr 2 CCl₃ —SO₂—(4-Me—Ph)4-478 Et H Me Me 0 CCl₃ —SO₂-(Thien-2-yl) 4-479 Et H Me Et 0 CCl₃—SO₂-(Thien-2-yl) 4-480 Et H Me n-Pr 0 CCl₃ —SO₂-(Thien-2-yl) 4-481 Et HMe Me 1 CCl₃ —SO₂-(Thien-2-yl) 4-482 Et H Me Et 1 CCl₃ —SO₂-(Thien-2-yl)4-483 Et H Me n-Pr 1 CCl₃ —SO₂-(Thien-2-yl) 4-484 Et H Me Me 2 CCl₃—SO₂-(Thien-2-yl) 4-485 Et H Me Et 2 CCl₃ —SO₂-(Thien-2-yl) 4-486 Et HMe n-Pr 2 CCl₃ —SO₂-(Thien-2-yl) 4-487 Et H Me Me 0 CCl₃ —CO—Ph 4-488 EtH Me Et 0 CCl₃ —CO—Ph 4-489 Et H Me n-Pr 0 CCl₃ —CO—Ph 4-490 Et H Me Me1 CCl₃ —CO—Ph 4-491 Et H Me Et 1 CCl₃ —CO—Ph 4-492 Et H Me n-Pr 1 CCl₃—CO—Ph 4-493 Et H Me Me 2 CCl₃ —CO—Ph 4-494 Et H Me Et 2 CCl₃ —CO—Ph4-495 Et H Me n-Pr 2 CCl₃ —CO—Ph 4-496 Et H Me Me 0 CCl₃ —CH₂—CO—Ph4-497 Et H Me Et 0 CCl₃ —CH₂—CO—Ph 4-498 Et H Me n-Pr 0 CCl₃ —CH₂—CO—Ph4-499 Et H Me Me 1 CCl₃ —CH₂—CO—Ph 4-500 Et H Me Et 1 CCl₃ —CH₂—CO—Ph4-501 Et H Me n-Pr 1 CCl₃ —CH₂—CO—Ph 4-502 Et H Me Me 2 CCl₃ —CH₂—CO—Ph4-503 Et H Me Et 2 CCl₃ —CH₂—CO—Ph 4-504 Et H Me n-Pr 2 CCl₃ —CH₂—CO—Ph4-505 Me Me Me Me 0 CCl₃ —SO₂—n-Pr 4-506 Me Me Me Et 0 CCl₃ —SO₂—n-Pr4-507 Me Me Me n-Pr 0 CCl₃ —SO₂—n-Pr 4-508 Me Me Me Me 1 CCl₃ —SO₂—n-Pr4-509 Me Me Me Et 1 CCl₃ —SO₂—n-Pr 4-510 Me Me Me n-Pr 1 CCl₃ —SO₂—n-Pr4-511 Me Me Me Me 2 CCl₃ —SO₂—n-Pr 4-512 Me Me Me Et 2 CCl₃ —SO₂—n-Pr4-513 Me Me Me n-Pr 2 CCl₃ —SO₂—n-Pr 4-514 Me Me Me Me 0 CCl₃—SO₂—(CH₂)₂OMe 4-515 Me Me Me Et 0 CCl₃ —SO₂—(CH₂)₂OMe 4-516 Me Me Men-Pr 0 CCl₃ —SO₂—(CH₂)₂OMe 4-517 Me Me Me Me 1 CCl₃ —SO₂—(CH₂)₂OMe 4-518Me Me Me Et 1 CCl₃ —SO₂—(CH₂)₂OMe 4-519 Me Me Me n-Pr 1 CCl₃—SO₂—(CH₂)₂OMe 4-520 Me Me Me Me 2 CCl₃ —SO₂—(CH₂)₂OMe 4-521 Me Me Me Et2 CCl₃ —SO₂—(CH₂)₂OMe 4-522 Me Me Me n-Pr 2 CCl₃ —SO₂—(CH₂)₂OMe 4-523 MeMe Me Me 0 CCl₃ —SO₂—Ph 4-524 Me Me Me Et 0 CCl₃ —SO₂—Ph 4-525 Me Me Men-Pr 0 CCl₃ —SO₂—Ph 4-526 Me Me Me Me 1 CCl₃ —SO₂—Ph 4-527 Me Me Me Et 1CCl₃ —SO₂—Ph 4-528 Me Me Me n-Pr 1 CCl₃ —SO₂—Ph 4-529 Me Me Me Me 2 CCl₃—SO₂—Ph 4-530 Me Me Me Et 2 CCl₃ —SO₂—Ph 4-531 Me Me Me n-Pr 2 CCl₃—SO₂—Ph 4-532 Me Me Me Me 0 CCl₃ —SO₂—(4-Me—Ph) 4-533 Me Me Me Et 0 CCl₃—SO₂—(4-Me—Ph) 4-534 Me Me Me n-Pr 0 CCl₃ —SO₂—(4-Me—Ph) 4-535 Me Me MeMe 1 CCl₃ —SO₂—(4-Me—Ph) 4-536 Me Me Me Et 1 CCl₃ —SO₂—(4-Me—Ph) 4-537Me Me Me n-Pr 1 CCl₃ —SO₂—(4-Me—Ph) 4-538 Me Me Me Me 2 CCl₃—SO₂—(4-Me—Ph) 4-539 Me Me Me Et 2 CCl₃ —SO₂—(4-Me—Ph) 4-540 Me Me Men-Pr 2 CCl₃ —SO₂—(4-Me—Ph) 4-541 Me Me Me Me 0 CCl₃ —SO₂-(Thien-2-yl)4-542 Me Me Me Et 0 CCl₃ —SO₂-(Thien-2-yl) 4-543 Me Me Me n-Pr 0 CCl₃—SO₂-(Thien-2-yl) 4-544 Me Me Me Me 1 CCl₃ —SO₂-(Thien-2-yl) 4-545 Me MeMe Et 1 CCl₃ —SO₂-(Thien-2-yl) 4-546 Me Me Me n-Pr 1 CCl₃—SO₂-(Thien-2-yl) 4-547 Me Me Me Me 2 CCl₃ —SO₂-(Thien-2-yl) 4-548 Me MeMe Et 2 CCl₃ —SO₂-(Thien-2-yl) 4-549 Me Me Me n-Pr 2 CCl₃—SO₂-(Thien-2-yl) 4-550 Me Me Me Me 0 CCl₃ —CO—Ph 4-551 Me Me Me Et 0CCl₃ —CO—Ph 4-552 Me Me Me n-Pr 0 CCl₃ —CO—Ph 4-553 Me Me Me Me 1 CCl₃—CO—Ph 4-554 Me Me Me Et 1 CCl₃ —CO—Ph 4-555 Me Me Me n-Pr 1 CCl₃ —CO—Ph4-556 Me Me Me Me 2 CCl₃ —CO—Ph 4-557 Me Me Me Et 2 CCl₃ —CO—Ph 4-558 MeMe Me n-Pr 2 CCl₃ —CO—Ph 4-559 Me Me Me Me 0 CCl₃ —CH₂—CO—Ph 4-560 Me MeMe Et 0 CCl₃ —CH₂—CO—Ph 4-561 Me Me Me n-Pr 0 CCl₃ —CH₂—CO—Ph 4-562 MeMe Me Me 1 CCl₃ —CH₂—CO—Ph 4-563 Me Me Me Et 1 CCl₃ —CH₂—CO—Ph 4-564 MeMe Me n-Pr 1 CCl₃ —CH₂—CO—Ph 4-565 Me Me Me Me 2 CCl₃ —CH₂—CO—Ph 4-566Me Me Me Et 2 CCl₃ —CH₂—CO—Ph 4-567 Me Me Me n-Pr 2 CCl₃ —CH₂—CO—Ph4-568 Me H Me Me 0 C₂F₅ —SO₂—n-Pr 4-569 Me H Me Et 0 C₂F₅ —SO₂—n-Pr4-570 Me H Me n-Pr 0 C₂F₅ —SO₂—n-Pr 4-571 Me H Me Me 1 C₂F₅ —SO₂—n-Pr4-572 Me H Me Et 1 C₂F₅ —SO₂—n-Pr 4-573 Me H Me n-Pr 1 C₂F₅ —SO₂—n-Pr4-574 Me H Me Me 2 C₂F₅ —SO₂—n-Pr 4-575 Me H Me Et 2 C₂F₅ —SO₂—n-Pr4-576 Me H Me n-Pr 2 C₂F₅ —SO₂—n-Pr 4-577 Me H Me Me 0 C₂F₅—SO₂—(CH₂)₂OMe 4-578 Me H Me Et 0 C₂F₅ —SO₂—(CH₂)₂OMe 4-579 Me H Me n-Pr0 C₂F₅ —SO₂—(CH₂)₂OMe 4-580 Me H Me Me 1 C₂F₅ —SO₂—(CH₂)₂OMe 4-581 Me HMe Et 1 C₂F₅ —SO₂—(CH₂)₂OMe 4-582 Me H Me n-Pr 1 C₂F₅ —SO₂—(CH₂)₂OMe4-583 Me H Me Me 2 C₂F₅ —SO₂—(CH₂)₂OMe 4-584 Me H Me Et 2 C₂F₅—SO₂—(CH₂)₂OMe 4-585 Me H Me n-Pr 2 C₂F₅ —SO₂—(CH₂)₂OMe 4-586 Me H Me Me0 C₂F₅ —SO₂—Ph 4-587 Me H Me Et 0 C₂F₅ —SO₂—Ph 4-588 Me H Me n-Pr 0 C₂F₅—SO₂—Ph 4-589 Me H Me Me 1 C₂F₅ —SO₂—Ph 4-590 Me H Me Et 1 C₂F₅ —SO₂—Ph4-591 Me H Me n-Pr 1 C₂F₅ —SO₂—Ph 4-592 Me H Me Me 2 C₂F₅ —SO₂—Ph 4-593Me H Me Et 2 C₂F₅ —SO₂—Ph 4-594 Me H Me n-Pr 2 C₂F₅ —SO₂—Ph 4-595 Me HMe Me 0 C₂F₅ —SO₂—(4-Me—Ph) 4-596 Me H Me Et 0 C₂F₅ —SO₂—(4-Me—Ph) 4-597Me H Me n-Pr 0 C₂F₅ —SO₂—(4-Me—Ph) 4-598 Me H Me Me 1 C₂F₅—SO₂—(4-Me—Ph) 4-599 Me H Me Et 1 C₂F₅ —SO₂—(4-Me—Ph) 4-600 Me H Me n-Pr1 C₂F₅ —SO₂—(4-Me—Ph) 4-601 Me H Me Me 2 C₂F₅ —SO₂—(4-Me—Ph) 4-602 Me HMe Et 2 C₂F₅ —SO₂—(4-Me—Ph) 4-603 Me H Me n-Pr 2 C₂F₅ —SO₂—(4-Me—Ph)4-604 Me H Me Me 0 C₂F₅ —SO₂-(Thien-2-yl) 4-605 Me H Me Et 0 C₂F₅—SO₂-(Thien-2-yl) 4-606 Me H Me n-Pr 0 C₂F₅ —SO₂-(Thien-2-yl) 4-607 Me HMe Me 1 C₂F₅ —SO₂-(Thien-2-yl) 4-608 Me H Me Et 1 C₂F₅ —SO₂-(Thien-2-yl)4-609 Me H Me n-Pr 1 C₂F₅ —SO₂-(Thien-2-yl) 4-610 Me H Me Me 2 C₂F₅—SO₂-(Thien-2-yl) 4-611 Me H Me Et 2 C₂F₅ —SO₂-(Thien-2-yl) 4-612 Me HMe n-Pr 2 C₂F₅ —SO₂-(Thien-2-yl) 4-613 Me H Me Me 0 C₂F₅ —CO—Ph 4-614 MeH Me Et 0 C₂F₅ —CO—Ph 4-615 Me H Me n-Pr 0 C₂F₅ —CO—Ph 4-616 Me H Me Me1 C₂F₅ —CO—Ph 4-617 Me H Me Et 1 C₂F₅ —CO—Ph 4-618 Me H Me n-Pr 1 C₂F₅—CO—Ph 4-619 Me H Me Me 2 C₂F₅ —CO—Ph 4-620 Me H Me Et 2 C₂F₅ —CO—Ph4-621 Me H Me n-Pr 2 C₂F₅ —CO—Ph 4-622 Me H Me Me 0 C₂F₅ —CH₂—CO—Ph4-623 Me H Me Et 0 C₂F₅ —CH₂—CO—Ph 4-624 Me H Me n-Pr 0 C₂F₅ —CH₂—CO—Ph4-625 Me H Me Me 1 C₂F₅ —CH₂—CO—Ph 4-626 Me H Me Et 1 C₂F₅ —CH₂—CO—Ph4-627 Me H Me n-Pr 1 C₂F₅ —CH₂—CO—Ph 4-628 Me H Me Me 2 C₂F₅ —CH₂—CO—Ph4-629 Me H Me Et 2 C₂F₅ —CH₂—CO—Ph 4-630 Me H Me n-Pr 2 C₂F₅ —CH₂—CO—Ph4-631 Et H Me Me 0 C₂F₅ —SO₂—n-Pr 4-632 Et H Me Et 0 C₂F₅ —SO₂—n-Pr4-633 Et H Me n-Pr 0 C₂F₅ —SO₂—n-Pr 4-634 Et H Me Me 1 C₂F₅ —SO₂—n-Pr4-635 Et H Me Et 1 C₂F₅ —SO₂—n-Pr 4-636 Et H Me n-Pr 1 C₂F₅ —SO₂—n-Pr4-637 Et H Me Me 2 C₂F₅ —SO₂—n-Pr 4-638 Et H Me Et 2 C₂F₅ —SO₂—n-Pr4-639 Et H Me n-Pr 2 C₂F₅ —SO₂—n-Pr 4-640 Et H Me Me 0 C₂F₅—SO₂—(CH₂)₂OMe 4-641 Et H Me Et 0 C₂F₅ —SO₂—(CH₂)₂OMe 4-642 Et H Me n-Pr0 C₂F₅ —SO₂—(CH₂)₂OMe 4-643 Et H Me Me 1 C₂F₅ —SO₂—(CH₂)₂OMe 4-644 Et HMe Et 1 C₂F₅ —SO₂—(CH₂)₂OMe 4-645 Et H Me n-Pr 1 C₂F₅ —SO₂—(CH₂)₂OMe4-646 Et H Me Me 2 C₂F₅ —SO₂—(CH₂)₂OMe 4-647 Et H Me Et 2 C₂F₅—SO₂—(CH₂)₂OMe 4-648 Et H Me n-Pr 2 C₂F₅ —SO₂—(CH₂)₂OMe 4-649 Et H Me Me0 C₂F₅ —SO₂—Ph 4-650 Et H Me Et 0 C₂F₅ —SO₂—Ph 4-651 Et H Me n-Pr 0 C₂F₅—SO₂—Ph 4-652 Et H Me Me 1 C₂F₅ —SO₂—Ph 4-653 Et H Me Et 1 C₂F₅ —SO₂—Ph4-654 Et H Me n-Pr 1 C₂F₅ —SO₂—Ph 4-655 Et H Me Me 2 C₂F₅ —SO₂—Ph 4-656Et H Me Et 2 C₂F₅ —SO₂—Ph 4-657 Et H Me n-Pr 2 C₂F₅ —SO₂—Ph 4-658 Et HMe Me 0 C₂F₅ —SO₂—(4-Me—Ph) 4-659 Et H Me Et 0 C₂F₅ —SO₂—(4-Me—Ph) 4-660Et H Me n-Pr 0 C₂F₅ —SO₂—(4-Me—Ph) 4-661 Et H Me Me 1 C₂F₅—SO₂—(4-Me—Ph) 4-662 Et H Me Et 1 C₂F₅ —SO₂—(4-Me—Ph) 4-663 Et H Me n-Pr1 C₂F₅ —SO₂—(4-Me—Ph) 4-664 Et H Me Me 2 C₂F₅ —SO₂—(4-Me—Ph) 4-665 Et HMe Et 2 C₂F₅ —SO₂—(4-Me—Ph) 4-666 Et H Me n-Pr 2 C₂F₅ —SO₂—(4-Me—Ph)4-667 Et H Me Me 0 C₂F₅ —SO₂-(Thien-2-yl) 4-668 Et H Me Et 0 C₂F₅—SO₂-(Thien-2-yl) 4-669 Et H Me n-Pr 0 C₂F₅ —SO₂-(Thien-2-yl) 4-670 Et HMe Me 1 C₂F₅ —SO₂-(Thien-2-yl) 4-671 Et H Me Et 1 C₂F₅ —SO₂-(Thien-2-yl)4-672 Et H Me n-Pr 1 C₂F₅ —SO₂-(Thien-2-yl) 4-673 Et H Me Me 2 C₂F₅—SO₂-(Thien-2-yl) 4-674 Et H Me Et 2 C₂F₅ —SO₂-(Thien-2-yl) 4-675 Et HMe n-Pr 2 C₂F₅ —SO₂-(Thien-2-yl) 4-676 Et H Me Me 0 C₂F₅ —CO—Ph 4-677 EtH Me Et 0 C₂F₅ —CO—Ph 4-678 Et H Me n-Pr 0 C₂F₅ —CO—Ph 4-679 Et H Me Me1 C₂F₅ —CO—Ph 4-680 Et H Me Et 1 C₂F₅ —CO—Ph 4-681 Et H Me n-Pr 1 C₂F₅—CO—Ph 4-682 Et H Me Me 2 C₂F₅ —CO—Ph 4-683 Et H Me Et 2 C₂F₅ —CO—Ph4-684 Et H Me n-Pr 2 C₂F₅ —CO—Ph 4-685 Et H Me Me 0 C₂F₅ —CH₂—CO—Ph4-686 Et H Me Et 0 C₂F₅ —CH₂—CO—Ph 4-687 Et H Me n-Pr 0 C₂F₅ —CH₂—CO—Ph4-688 Et H Me Me 1 C₂F₅ —CH₂—CO—Ph 4-689 Et H Me Et 1 C₂F₅ —CH₂—CO—Ph4-690 Et H Me n-Pr 1 C₂F₅ —CH₂—CO—Ph 4-691 Et H Me Me 2 C₂F₅ —CH₂—CO—Ph4-692 Et H Me Et 2 C₂F₅ —CH₂—CO—Ph 4-693 Et H Me n-Pr 2 C₂F₅ —CH₂—CO—Ph4-694 Me Me Me Me 0 C₂F₅ —SO₂—n-Pr 4-695 Me Me Me Et 0 C₂F₅ —SO₂—n-Pr4-696 Me Me Me n-Pr 0 C₂F₅ —SO₂—n-Pr 4-697 Me Me Me Me 1 C₂F₅ —SO₂—n-Pr4-698 Me Me Me Et 1 C₂F₅ —SO₂—n-Pr 4-699 Me Me Me n-Pr 1 C₂F₅ —SO₂—n-Pr4-700 Me Me Me Me 2 C₂F₅ —SO₂—n-Pr 4-701 Me Me Me Et 2 C₂F₅ —SO₂—n-Pr4-702 Me Me Me n-Pr 2 C₂F₅ —SO₂—n-Pr 4-703 Me Me Me Me 0 C₂F₅—SO₂—(CH₂)₂OMe 4-704 Me Me Me Et 0 C₂F₅ —SO₂—(CH₂)₂OMe 4-705 Me Me Men-Pr 0 C₂F₅ —SO₂—(CH₂)₂OMe 4-706 Me Me Me Me 1 C₂F₅ —SO₂—(CH₂)₂OMe 4-707Me Me Me Et 1 C₂F₅ —SO₂—(CH₂)₂OMe 4-708 Me Me Me n-Pr 1 C₂F₅—SO₂—(CH₂)₂OMe 4-709 Me Me Me Me 2 C₂F₅ —SO₂—(CH₂)₂OMe 4-710 Me Me Me Et2 C₂F₅ —SO₂—(CH₂)₂OMe 4-711 Me Me Me n-Pr 2 C₂F₅ —SO₂—(CH₂)₂OMe 4-712 MeMe Me Me 0 C₂F₅ —SO₂—Ph 4-713 Me Me Me Et 0 C₂F₅ —SO₂—Ph 4-714 Me Me Men-Pr 0 C₂F₅ —SO₂—Ph 4-715 Me Me Me Me 1 C₂F₅ —SO₂—Ph 4-716 Me Me Me Et 1C₂F₅ —SO₂—Ph 4-717 Me Me Me n-Pr 1 C₂F₅ —SO₂—Ph 4-718 Me Me Me Me 2 C₂F₅—SO₂—Ph 4-719 Me Me Me Et 2 C₂F₅ —SO₂—Ph 4-720 Me Me Me n-Pr 2 C₂F₅—SO₂—Ph 4-721 Me Me Me Me 0 C₂F₅ —SO₂—(4-Me—Ph) 4-722 Me Me Me Et 0 C₂F₅—SO₂—(4-Me—Ph) 4-723 Me Me Me n-Pr 0 C₂F₅ —SO₂—(4-Me—Ph) 4-724 Me Me MeMe 1 C₂F₅ —SO₂—(4-Me—Ph) 4-725 Me Me Me Et 1 C₂F₅ —SO₂—(4-Me—Ph) 4-726Me Me Me n-Pr 1 C₂F₅ —SO₂—(4-Me—Ph) 4-727 Me Me Me Me 2 C₂F₅—SO₂—(4-Me—Ph) 4-728 Me Me Me Et 2 C₂F₅ —SO₂—(4-Me—Ph) 4-729 Me Me Men-Pr 2 C₂F₅ —SO₂—(4-Me—Ph) 4-730 Me Me Me Me 0 C₂F₅ —SO₂-(Thien-2-yl)4-731 Me Me Me Et 0 C₂F₅ —SO₂-(Thien-2-yl) 4-732 Me Me Me n-Pr 0 C₂F₅—SO₂-(Thien-2-yl) 4-733 Me Me Me Me 1 C₂F₅ —SO₂-(Thien-2-yl) 4-734 Me MeMe Et 1 C₂F₅ —SO₂-(Thien-2-yl) 4-735 Me Me Me n-Pr 1 C₂F₅—SO₂-(Thien-2-yl) 4-736 Me Me Me Me 2 C₂F₅ —SO₂-(Thien-2-yl) 4-737 Me MeMe Et 2 C₂F₅ —SO₂-(Thien-2-yl) 4-738 Me Me Me n-Pr 2 C₂F₅—SO₂-(Thien-2-yl) 4-739 Me Me Me Me 0 C₂F₅ —CO—Ph 4-740 Me Me Me Et 0C₂F₅ —CO—Ph 4-741 Me Me Me n-Pr 0 C₂F₅ —CO—Ph 4-742 Me Me Me Me 1 C₂F₅—CO—Ph 4-743 Me Me Me Et 1 C₂F₅ —CO—Ph 4-744 Me Me Me n-Pr 1 C₂F₅ —CO—Ph4-745 Me Me Me Me 2 C₂F₅ —CO—Ph 4-746 Me Me Me Et 2 C₂F₅ —CO—Ph 4-747 MeMe Me n-Pr 2 C₂F₅ —CO—Ph 4-748 Me Me Me Me 0 C₂F₅ —CH₂—CO—Ph 4-749 Me MeMe Et 0 C₂F₅ —CH₂—CO—Ph 4-750 Me Me Me n-Pr 0 C₂F₅ —CH₂—CO—Ph 4-751 MeMe Me Me 1 C₂F₅ —CH₂—CO—Ph 4-752 Me Me Me Et 1 C₂F₅ —CH₂—CO—Ph 4-753 MeMe Me n-Pr 1 C₂F₅ —CH₂—CO—Ph 4-754 Me Me Me Me 2 C₂F₅ —CH₂—CO—Ph 4-755Me Me Me Et 2 C₂F₅ —CH₂—CO—Ph 4-756 Me Me Me n-Pr 2 C₂F₅ —CH₂—CO—Ph4-757 Me H Me Me 0 CF(CF₃)₂ —SO₂—n-Pr 4-758 Me H Me Et 0 CF(CF₃)₂—SO₂—n-Pr 4-759 Me H Me n-Pr 0 CF(CF₃)₂ —SO₂—n-Pr 4-760 Me H Me Me 1CF(CF₃)₂ —SO₂—n-Pr 4-761 Me H Me Et 1 CF(CF₃)₂ —SO₂—n-Pr 4-762 Me H Men-Pr 1 CF(CF₃)₂ —SO₂—n-Pr 4-763 Me H Me Me 2 CF(CF₃)₂ —SO₂—n-Pr 4-764 MeH Me Et 2 CF(CF₃)₂ —SO₂—n-Pr 4-765 Me H Me n-Pr 2 CF(CF₃)₂ —SO₂—n-Pr4-766 Me H Me Me 0 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-767 Me H Me Et 0 CF(CF₃)₂—SO₂—(CH₂)₂OMe 4-768 Me H Me n-Pr 0 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-769 Me HMe Me 1 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-770 Me H Me Et 1 CF(CF₃)₂—SO₂—(CH₂)₂OMe 4-771 Me H Me n-Pr 1 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-772 Me HMe Me 2 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-773 Me H Me Et 2 CF(CF₃)₂—SO₂—(CH₂)₂OMe 4-774 Me H Me n-Pr 2 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-775 Me HMe Me 0 CF(CF₃)₂ —SO₂—Ph 4-776 Me H Me Et 0 CF(CF₃)₂ —SO₂—Ph 4-777 Me HMe n-Pr 0 CF(CF₃)₂ —SO₂—Ph 4-778 Me H Me Me 1 CF(CF₃)₂ —SO₂—Ph 4-779 MeH Me Et 1 CF(CF₃)₂ —SO₂—Ph 4-780 Me H Me n-Pr 1 CF(CF₃)₂ —SO₂—Ph 4-781Me H Me Me 2 CF(CF₃)₂ —SO₂—Ph 4-782 Me H Me Et 2 CF(CF₃)₂ —SO₂—Ph 4-783Me H Me n-Pr 2 CF(CF₃)₂ —SO₂—Ph 4-784 Me H Me Me 0 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-785 Me H Me Et 0 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-786 Me H Men-Pr 0 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-787 Me H Me Me 1 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-788 Me H Me Et 1 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-789 Me H Men-Pr 1 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-790 Me H Me Me 2 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-791 Me H Me Et 2 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-792 Me H Men-Pr 2 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-793 Me H Me Me 0 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-794 Me H Me Et 0 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-795 MeH Me n-Pr 0 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-796 Me H Me Me 1 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-797 Me H Me Et 1 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-798 MeH Me n-Pr 1 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-799 Me H Me Me 2 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-800 Me H Me Et 2 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-801 MeH Me n-Pr 2 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-802 Me H Me Me 0 CF(CF₃)₂—CO—Ph 4-803 Me H Me Et 0 CF(CF₃)₂ —CO—Ph 4-804 Me H Me n-Pr 0 CF(CF₃)₂—CO—Ph 4-805 Me H Me Me 1 CF(CF₃)₂ —CO—Ph 4-806 Me H Me Et 1 CF(CF₃)₂—CO—Ph 4-807 Me H Me n-Pr 1 CF(CF₃)₂ —CO—Ph 4-808 Me H Me Me 2 CF(CF₃)₂—CO—Ph 4-809 Me H Me Et 2 CF(CF₃)₂ —CO—Ph 4-810 Me H Me n-Pr 2 CF(CF₃)₂—CO—Ph 4-811 Me H Me Me 0 CF(CF₃)₂ —CH₂—CO—Ph 4-812 Me H Me Et 0CF(CF₃)₂ —CH₂—CO—Ph 4-813 Me H Me n-Pr 0 CF(CF₃)₂ —CH₂—CO—Ph 4-814 Me HMe Me 1 CF(CF₃)₂ —CH₂—CO—Ph 4-815 Me H Me Et 1 CF(CF₃)₂ —CH₂—CO—Ph 4-816Me H Me n-Pr 1 CF(CF₃)₂ —CH₂—CO—Ph 4-817 Me H Me Me 2 CF(CF₃)₂—CH₂—CO—Ph 4-818 Me H Me Et 2 CF(CF₃)₂ —CH₂—CO—Ph 4-819 Me H Me n-Pr 2CF(CF₃)₂ —CH₂—CO—Ph 4-820 Et H Me Me 0 CF(CF₃)₂ —SO₂—n-Pr 4-821 Et H MeEt 0 CF(CF₃)₂ —SO₂—n-Pr 4-822 Et H Me n-Pr 0 CF(CF₃)₂ —SO₂—n-Pr 4-823 EtH Me Me 1 CF(CF₃)₂ —SO₂—n-Pr 4-824 Et H Me Et 1 CF(CF₃)₂ —SO₂—n-Pr 4-825Et H Me n-Pr 1 CF(CF₃)₂ —SO₂—n-Pr 4-826 Et H Me Me 2 CF(CF₃)₂ —SO₂—n-Pr4-827 Et H Me Et 2 CF(CF₃)₂ —SO₂—n-Pr 4-828 Et H Me n-Pr 2 CF(CF₃)₂—SO₂—n-Pr 4-829 Et H Me Me 0 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-830 Et H Me Et 0CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-831 Et H Me n-Pr 0 CF(CF₃)₂ —SO₂—(CH₂)₂OMe4-832 Et H Me Me 1 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-833 Et H Me Et 1 CF(CF₃)₂—SO₂—(CH₂)₂OMe 4-834 Et H Me n-Pr 1 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-835 Et HMe Me 2 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-836 Et H Me Et 2 CF(CF₃)₂—SO₂—(CH₂)₂OMe 4-837 Et H Me n-Pr 2 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-838 Et HMe Me 0 CF(CF₃)₂ —SO₂—Ph 4-839 Et H Me Et 0 CF(CF₃)₂ —SO₂—Ph 4-840 Et HMe n-Pr 0 CF(CF₃)₂ —SO₂—Ph 4-841 Et H Me Me 1 CF(CF₃)₂ —SO₂—Ph 4-842 EtH Me Et 1 CF(CF₃)₂ —SO₂—Ph 4-843 Et H Me n-Pr 1 CF(CF₃)₂ —SO₂—Ph 4-844Et H Me Me 2 CF(CF₃)₂ —SO₂—Ph 4-845 Et H Me Et 2 CF(CF₃)₂ —SO₂—Ph 4-846Et H Me n-Pr 2 CF(CF₃)₂ —SO₂—Ph 4-847 Et H Me Me 0 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-848 Et H Me Et 0 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-849 Et H Men-Pr 0 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-850 Et H Me Me 1 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-851 Et H Me Et 1 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-852 Et H Men-Pr 1 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-853 Et H Me Me 2 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-854 Et H Me Et 2 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-855 Et H Men-Pr 2 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-856 Et H Me Me 0 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-857 Et H Me Et 0 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-858 EtH Me n-Pr 0 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-859 Et H Me Me 1 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-860 Et H Me Et 1 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-861 EtH Me n-Pr 1 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-862 Et H Me Me 2 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-863 Et H Me Et 2 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-864 EtH Me n-Pr 2 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-865 Et H Me Me 0 CF(CF₃)₂—CO—Ph 4-866 Et H Me Et 0 CF(CF₃)₂ —CO—Ph 4-867 Et H Me n-Pr 0 CF(CF₃)₂—CO—Ph 4-868 Et H Me Me 1 CF(CF₃)₂ —CO—Ph 4-869 Et H Me Et 1 CF(CF₃)₂—CO—Ph 4-870 Et H Me n-Pr 1 CF(CF₃)₂ —CO—Ph 4-871 Et H Me Me 2 CF(CF₃)₂—CO—Ph 4-872 Et H Me Et 2 CF(CF₃)₂ —CO—Ph 4-873 Et H Me n-Pr 2 CF(CF₃)₂—CO—Ph 4-874 Et H Me Me 0 CF(CF₃)₂ —CH₂—CO—Ph 4-875 Et H Me Et 0CF(CF₃)₂ —CH₂—CO—Ph 4-876 Et H Me n-Pr 0 CF(CF₃)₂ —CH₂—CO—Ph 4-877 Et HMe Me 1 CF(CF₃)₂ —CH₂—CO—Ph 4-878 Et H Me Et 1 CF(CF₃)₂ —CH₂—CO—Ph 4-879Et H Me n-Pr 1 CF(CF₃)₂ —CH₂—CO—Ph 4-880 Et H Me Me 2 CF(CF₃)₂—CH₂—CO—Ph 4-881 Et H Me Et 2 CF(CF₃)₂ —CH₂—CO—Ph 4-882 Et H Me n-Pr 2CF(CF₃)₂ —CH₂—CO—Ph 4-883 Me Me Me Me 0 CF(CF₃)₂ —SO₂—n-Pr 4-884 Me MeMe Et 0 CF(CF₃)₂ —SO₂—n-Pr 4-885 Me Me Me n-Pr 0 CF(CF₃)₂ —SO₂—n-Pr4-886 Me Me Me Me 1 CF(CF₃)₂ —SO₂—n-Pr 4-887 Me Me Me Et 1 CF(CF₃)₂—SO₂—n-Pr 4-888 Me Me Me n-Pr 1 CF(CF₃)₂ —SO₂—n-Pr 4-889 Me Me Me Me 2CF(CF₃)₂ —SO₂—n-Pr 4-890 Me Me Me Et 2 CF(CF₃)₂ —SO₂—n-Pr 4-891 Me Me Men-Pr 2 CF(CF₃)₂ —SO₂—n-Pr 4-892 Me Me Me Me 0 CF(CF₃)₂ —SO₂—(CH₂)₂OMe4-893 Me Me Me Et 0 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-894 Me Me Me n-Pr 0CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-895 Me Me Me Me 1 CF(CF₃)₂ —SO₂—(CH₂)₂OMe4-896 Me Me Me Et 1 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-897 Me Me Me n-Pr 1CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-898 Me Me Me Me 2 CF(CF₃)₂ —SO₂—(CH₂)₂OMe4-899 Me Me Me Et 2 CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-900 Me Me Me n-Pr 2CF(CF₃)₂ —SO₂—(CH₂)₂OMe 4-901 Me Me Me Me 0 CF(CF₃)₂ —SO₂—Ph 4-902 Me MeMe Et 0 CF(CF₃)₂ —SO₂—Ph 4-903 Me Me Me n-Pr 0 CF(CF₃)₂ —SO₂—Ph 4-904 MeMe Me Me 1 CF(CF₃)₂ —SO₂—Ph 4-905 Me Me Me Et 1 CF(CF₃)₂ —SO₂—Ph 4-906Me Me Me n-Pr 1 CF(CF₃)₂ —SO₂—Ph 4-907 Me Me Me Me 2 CF(CF₃)₂ —SO₂—Ph4-908 Me Me Me Et 2 CF(CF₃)₂ —SO₂—Ph 4-909 Me Me Me n-Pr 2 CF(CF₃)₂—SO₂—Ph 4-910 Me Me Me Me 0 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-911 Me Me Me Et 0CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-912 Me Me Me n-Pr 0 CF(CF₃)₂ —SO₂—(4-Me—Ph)4-913 Me Me Me Me 1 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-914 Me Me Me Et 1 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-915 Me Me Me n-Pr 1 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-916 Me MeMe Me 2 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-917 Me Me Me Et 2 CF(CF₃)₂—SO₂—(4-Me—Ph) 4-918 Me Me Me n-Pr 2 CF(CF₃)₂ —SO₂—(4-Me—Ph) 4-919 Me MeMe Me 0 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-920 Me Me Me Et 0 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-921 Me Me Me n-Pr 0 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-922Me Me Me Me 1 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-923 Me Me Me Et 1 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-924 Me Me Me n-Pr 1 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-925Me Me Me Me 2 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-926 Me Me Me Et 2 CF(CF₃)₂—SO₂-(Thien-2-yl) 4-927 Me Me Me n-Pr 2 CF(CF₃)₂ —SO₂-(Thien-2-yl) 4-928Me Me Me Me 0 CF(CF₃)₂ —CO—Ph 4-929 Me Me Me Et 0 CF(CF₃)₂ —CO—Ph 4-930Me Me Me n-Pr 0 CF(CF₃)₂ —CO—Ph 4-931 Me Me Me Me 1 CF(CF₃)₂ —CO—Ph4-932 Me Me Me Et 1 CF(CF₃)₂ —CO—Ph 4-933 Me Me Me n-Pr 1 CF(CF₃)₂—CO—Ph 4-934 Me Me Me Me 2 CF(CF₃)₂ —CO—Ph 4-935 Me Me Me Et 2 CF(CF₃)₂—CO—Ph 4-936 Me Me Me n-Pr 2 CF(CF₃)₂ —CO—Ph 4-937 Me Me Me Me 0CF(CF₃)₂ —CH₂—CO—Ph 4-938 Me Me Me Et 0 CF(CF₃)₂ —CH₂—CO—Ph 4-939 Me MeMe n-Pr 0 CF(CF₃)₂ —CH₂—CO—Ph 4-940 Me Me Me Me 1 CF(CF₃)₂ —CH₂—CO—Ph4-941 Me Me Me Et 1 CF(CF₃)₂ —CH₂—CO—Ph 4-942 Me Me Me n-Pr 1 CF(CF₃)₂—CH₂—CO—Ph 4-943 Me Me Me Me 2 CF(CF₃)₂ —CH₂—CO—Ph 4-944 Me Me Me Et 2CF(CF₃)₂ —CH₂—CO—Ph 4-945 Me Me Me n-Pr 2 CF(CF₃)₂ —CH₂—CO—Ph 4-946 Me HMe Me 0 CHF₂ —SO₂—n-Pr 4-947 Me H Me Et 0 CHF₂ —SO₂—n-Pr 4-948 Me H Men-Pr 0 CHF₂ —SO₂—n-Pr 4-949 Me H Me Me 1 CHF₂ —SO₂—n-Pr 4-950 Me H Me Et1 CHF₂ —SO₂—n-Pr 4-951 Me H Me n-Pr 1 CHF₂ —SO₂—n-Pr 4-952 Me H Me Me 2CHF₂ —SO₂—n-Pr 4-953 Me H Me Et 2 CHF₂ —SO₂—n-Pr 4-954 Me H Me n-Pr 2CHF₂ —SO₂—n-Pr 4-955 Me H Me Me 0 CHF₂ —SO₂—(CH₂)₂OMe 4-956 Me H Me Et 0CHF₂ —SO₂—(CH₂)₂OMe 4-957 Me H Me n-Pr 0 CHF₂ —SO₂—(CH₂)₂OMe 4-958 Me HMe Me 1 CHF₂ —SO₂—(CH₂)₂OMe 4-959 Me H Me Et 1 CHF₂ —SO₂—(CH₂)₂OMe 4-960Me H Me n-Pr 1 CHF₂ —SO₂—(CH₂)₂OMe 4-961 Me H Me Me 2 CHF₂—SO₂—(CH₂)₂OMe 4-962 Me H Me Et 2 CHF₂ —SO₂—(CH₂)₂OMe 4-963 Me H Me n-Pr2 CHF₂ —SO₂—(CH₂)₂OMe 4-964 Me H Me Me 0 CHF₂ —SO₂—Ph 4-965 Me H Me Et 0CHF₂ —SO₂—Ph 4-966 Me H Me n-Pr 0 CHF₂ —SO₂—Ph 4-967 Me H Me Me 1 CHF₂—SO₂—Ph 4-968 Me H Me Et 1 CHF₂ —SO₂—Ph 4-969 Me H Me n-Pr 1 CHF₂—SO₂—Ph 4-970 Me H Me Me 2 CHF₂ —SO₂—Ph 4-971 Me H Me Et 2 CHF₂ —SO₂—Ph4-972 Me H Me n-Pr 2 CHF₂ —SO₂—Ph 4-973 Me H Me Me 0 CHF₂ —SO₂—(4-Me—Ph)4-974 Me H Me Et 0 CHF₂ —SO₂—(4-Me—Ph) 4-975 Me H Me n-Pr 0 CHF₂—SO₂—(4-Me—Ph) 4-976 Me H Me Me 1 CHF₂ —SO₂—(4-Me—Ph) 4-977 Me H Me Et 1CHF₂ —SO₂—(4-Me—Ph) 4-978 Me H Me n-Pr 1 CHF₂ —SO₂—(4-Me—Ph) 4-979 Me HMe Me 2 CHF₂ —SO₂—(4-Me—Ph) 4-980 Me H Me Et 2 CHF₂ —SO₂—(4-Me—Ph) 4-981Me H Me n-Pr 2 CHF₂ —SO₂—(4-Me—Ph) 4-982 Me H Me Me 0 CHF₂—SO₂-(Thien-2-yl) 4-983 Me H Me Et 0 CHF₂ —SO₂-(Thien-2-yl) 4-984 Me HMe n-Pr 0 CHF₂ —SO₂-(Thien-2-yl) 4-985 Me H Me Me 1 CHF₂—SO₂-(Thien-2-yl) 4-986 Me H Me Et 1 CHF₂ —SO₂-(Thien-2-yl) 4-987 Me HMe n-Pr 1 CHF₂ —SO₂-(Thien-2-yl) 4-988 Me H Me Me 2 CHF₂—SO₂-(Thien-2-yl) 4-989 Me H Me Et 2 CHF₂ —SO₂-(Thien-2-yl) 4-990 Me HMe n-Pr 2 CHF₂ —SO₂-(Thien-2-yl) 4-991 Me H Me Me 0 CHF₂ —CO—Ph 4-992 MeH Me Et 0 CHF₂ —CO—Ph 4-993 Me H Me n-Pr 0 CHF₂ —CO—Ph 4-994 Me H Me Me1 CHF₂ —CO—Ph 4-995 Me H Me Et 1 CHF₂ —CO—Ph 4-996 Me H Me n-Pr 1 CHF₂—CO—Ph 4-997 Me H Me Me 2 CHF₂ —CO—Ph 4-998 Me H Me Et 2 CHF₂ —CO—Ph4-999 Me H Me n-Pr 2 CHF₂ —CO—Ph 4-1000 Me H Me Me 0 CHF₂ —CH₂—CO—Ph4-1001 Me H Me Et 0 CHF₂ —CH₂—CO—Ph 4-1002 Me H Me n-Pr 0 CHF₂—CH₂—CO—Ph 4-1003 Me H Me Me 1 CHF₂ —CH₂—CO—Ph 4-1004 Me H Me Et 1 CHF₂—CH₂—CO—Ph 4-1005 Me H Me n-Pr 1 CHF₂ —CH₂—CO—Ph 4-1006 Me H Me Me 2CHF₂ —CH₂—CO—Ph 4-1007 Me H Me Et 2 CHF₂ —CH₂—CO—Ph 4-1008 Me H Me n-Pr2 CHF₂ —CH₂—CO—Ph 4-1009 Et H Me Me 0 CHF₂ —SO₂—n-Pr 4-1010 Et H Me Et 0CHF₂ —SO₂—n-Pr 4-1011 Et H Me n-Pr 0 CHF₂ —SO₂—n-Pr 4-1012 Et H Me Me 1CHF₂ —SO₂—n-Pr 4-1013 Et H Me Et 1 CHF₂ —SO₂—n-Pr 4-1014 Et H Me n-Pr 1CHF₂ —SO₂—n-Pr 4-1015 Et H Me Me 2 CHF₂ —SO₂—n-Pr 4-1016 Et H Me Et 2CHF₂ —SO₂—n-Pr 4-1017 Et H Me n-Pr 2 CHF₂ —SO₂—n-Pr 4-1018 Et H Me Me 0CHF₂ —SO₂—(CH₂)₂OMe 4-1019 Et H Me Et 0 CHF₂ —SO₂—(CH₂)₂OMe 4-1020 Et HMe n-Pr 0 CHF₂ —SO₂—(CH₂)₂OMe 4-1021 Et H Me Me 1 CHF₂ —SO₂—(CH₂)₂OMe4-1022 Et H Me Et 1 CHF₂ —SO₂—(CH₂)₂OMe 4-1023 Et H Me n-Pr 1 CHF₂—SO₂—(CH₂)₂OMe 4-1024 Et H Me Me 2 CHF₂ —SO₂—(CH₂)₂OMe 4-1025 Et H Me Et2 CHF₂ —SO₂—(CH₂)₂OMe 4-1026 Et H Me n-Pr 2 CHF₂ —SO₂—(CH₂)₂OMe 4-1027Et H Me Me 0 CHF₂ —SO₂—Ph 4-1028 Et H Me Et 0 CHF₂ —SO₂—Ph 4-1029 Et HMe n-Pr 0 CHF₂ —SO₂—Ph 4-1030 Et H Me Me 1 CHF₂ —SO₂—Ph 4-1031 Et H MeEt 1 CHF₂ —SO₂—Ph 4-1032 Et H Me n-Pr 1 CHF₂ —SO₂—Ph 4-1033 Et H Me Me 2CHF₂ —SO₂—Ph 4-1034 Et H Me Et 2 CHF₂ —SO₂—Ph 4-1035 Et H Me n-Pr 2 CHF₂—SO₂—Ph 4-1036 Et H Me Me 0 CHF₂ —SO₂—(4-Me—Ph) 4-1037 Et H Me Et 0 CHF₂—SO₂—(4-Me—Ph) 4-1038 Et H Me n-Pr 0 CHF₂ —SO₂—(4-Me—Ph) 4-1039 Et H MeMe 1 CHF₂ —SO₂—(4-Me—Ph) 4-1040 Et H Me Et 1 CHF₂ —SO₂—(4-Me—Ph) 4-1041Et H Me n-Pr 1 CHF₂ —SO₂—(4-Me—Ph) 4-1042 Et H Me Me 2 CHF₂—SO₂—(4-Me—Ph) 4-1043 Et H Me Et 2 CHF₂ —SO₂—(4-Me—Ph) 4-1044 Et H Men-Pr 2 CHF₂ —SO₂—(4-Me—Ph) 4-1045 Et H Me Me 0 CHF₂ —SO₂-(Thien-2-yl)4-1046 Et H Me Et 0 CHF₂ —SO₂-(Thien-2-yl) 4-1047 Et H Me n-Pr 0 CHF₂—SO₂-(Thien-2-yl) 4-1048 Et H Me Me 1 CHF₂ —SO₂-(Thien-2-yl) 4-1049 Et HMe Et 1 CHF₂ —SO₂-(Thien-2-yl) 4-1050 Et H Me n-Pr 1 CHF₂—SO₂-(Thien-2-yl) 4-1051 Et H Me Me 2 CHF₂ —SO₂-(Thien-2-yl) 4-1052 Et HMe Et 2 CHF₂ —SO₂-(Thien-2-yl) 4-1053 Et H Me n-Pr 2 CHF₂—SO₂-(Thien-2-yl) 4-1054 Et H Me Me 0 CHF₂ —CO—Ph 4-1055 Et H Me Et 0CHF₂ —CO—Ph 4-1056 Et H Me n-Pr 0 CHF₂ —CO—Ph 4-1057 Et H Me Me 1 CHF₂—CO—Ph 4-1058 Et H Me Et 1 CHF₂ —CO—Ph 4-1059 Et H Me n-Pr 1 CHF₂ —CO—Ph4-1060 Et H Me Me 2 CHF₂ —CO—Ph 4-1061 Et H Me Et 2 CHF₂ —CO—Ph 4-1062Et H Me n-Pr 2 CHF₂ —CO—Ph 4-1063 Et H Me Me 0 CHF₂ —CH₂—CO—Ph 4-1064 EtH Me Et 0 CHF₂ —CH₂—CO—Ph 4-1065 Et H Me n-Pr 0 CHF₂ —CH₂—CO—Ph 4-1066Et H Me Me 1 CHF₂ —CH₂—CO—Ph 4-1067 Et H Me Et 1 CHF₂ —CH₂—CO—Ph 4-1068Et H Me n-Pr 1 CHF₂ —CH₂—CO—Ph 4-1069 Et H Me Me 2 CHF₂ —CH₂—CO—Ph4-1070 Et H Me Et 2 CHF₂ —CH₂—CO—Ph 4-1071 Et H Me n-Pr 2 CHF₂—CH₂—CO—Ph 4-1072 Me Me Me Me 0 CHF₂ —SO₂—n-Pr 4-1073 Me Me Me Et 0 CHF₂—SO₂—n-Pr 4-1074 Me Me Me n-Pr 0 CHF₂ —SO₂—n-Pr 4-1075 Me Me Me Me 1CHF₂ —SO₂—n-Pr 4-1076 Me Me Me Et 1 CHF₂ —SO₂—n-Pr 4-1077 Me Me Me n-Pr1 CHF₂ —SO₂—n-Pr 4-1078 Me Me Me Me 2 CHF₂ —SO₂—n-Pr 4-1079 Me Me Me Et2 CHF₂ —SO₂—n-Pr 4-1080 Me Me Me n-Pr 2 CHF₂ —SO₂—n-Pr 4-1081 Me Me MeMe 0 CHF₂ —SO₂—(CH₂)₂OMe 4-1082 Me Me Me Et 0 CHF₂ —SO₂—(CH₂)₂OMe 4-1083Me Me Me n-Pr 0 CHF₂ —SO₂—(CH₂)₂OMe 4-1084 Me Me Me Me 1 CHF₂—SO₂—(CH₂)₂OMe 4-1085 Me Me Me Et 1 CHF₂ —SO₂—(CH₂)₂OMe 4-1086 Me Me Men-Pr 1 CHF₂ —SO₂—(CH₂)₂OMe 4-1087 Me Me Me Me 2 CHF₂ —SO₂—(CH₂)₂OMe4-1088 Me Me Me Et 2 CHF₂ —SO₂—(CH₂)₂OMe 4-1089 Me Me Me n-Pr 2 CHF₂—SO₂—(CH₂)₂OMe 4-1090 Me Me Me Me 0 CHF₂ —SO₂—Ph 4-1091 Me Me Me Et 0CHF₂ —SO₂—Ph 4-1092 Me Me Me n-Pr 0 CHF₂ —SO₂—Ph 4-1093 Me Me Me Me 1CHF₂ —SO₂—Ph 4-1094 Me Me Me Et 1 CHF₂ —SO₂—Ph 4-1095 Me Me Me n-Pr 1CHF₂ —SO₂—Ph 4-1096 Me Me Me Me 2 CHF₂ —SO₂—Ph 4-1097 Me Me Me Et 2 CHF₂—SO₂—Ph 4-1098 Me Me Me n-Pr 2 CHF₂ —SO₂—Ph 4-1099 Me Me Me Me 0 CHF₂—SO₂—(4-Me—Ph) 4-1100 Me Me Me Et 0 CHF₂ —SO₂—(4-Me—Ph) 4-1101 Me Me Men-Pr 0 CHF₂ —SO₂—(4-Me—Ph) 4-1102 Me Me Me Me 1 CHF₂ —SO₂—(4-Me—Ph)4-1103 Me Me Me Et 1 CHF₂ —SO₂—(4-Me—Ph) 4-1104 Me Me Me n-Pr 1 CHF₂—SO₂—(4-Me—Ph) 4-1105 Me Me Me Me 2 CHF₂ —SO₂—(4-Me—Ph) 4-1106 Me Me MeEt 2 CHF₂ —SO₂—(4-Me—Ph) 4-1107 Me Me Me n-Pr 2 CHF₂ —SO₂—(4-Me—Ph)4-1108 Me Me Me Me 0 CHF₂ —SO₂-(Thien-2-yl) 4-1109 Me Me Me Et 0 CHF₂—SO₂-(Thien-2-yl) 4-1110 Me Me Me n-Pr 0 CHF₂ —SO₂-(Thien-2-yl) 4-1111Me Me Me Me 1 CHF₂ —SO₂-(Thien-2-yl) 4-1112 Me Me Me Et 1 CHF₂—SO₂-(Thien-2-yl) 4-1113 Me Me Me n-Pr 1 CHF₂ —SO₂-(Thien-2-yl) 4-1114Me Me Me Me 2 CHF₂ —SO₂-(Thien-2-yl) 4-1115 Me Me Me Et 2 CHF₂—SO₂-(Thien-2-yl) 4-1116 Me Me Me n-Pr 2 CHF₂ —SO₂-(Thien-2-yl) 4-1117Me Me Me Me 0 CHF₂ —CO—Ph 4-1118 Me Me Me Et 0 CHF₂ —CO—Ph 4-1119 Me MeMe n-Pr 0 CHF₂ —CO—Ph 4-1120 Me Me Me Me 1 CHF₂ —CO—Ph 4-1121 Me Me MeEt 1 CHF₂ —CO—Ph 4-1122 Me Me Me n-Pr 1 CHF₂ —CO—Ph 4-1123 Me Me Me Me 2CHF₂ —CO—Ph 4-1124 Me Me Me Et 2 CHF₂ —CO—Ph 4-1125 Me Me Me n-Pr 2 CHF₂—CO—Ph 4-1126 Me Me Me Me 0 CHF₂ —CH₂—CO—Ph 4-1127 Me Me Me Et 0 CHF₂—CH₂—CO—Ph 4-1128 Me Me Me n-Pr 0 CHF₂ —CH₂—CO—Ph 4-1129 Me Me Me Me 1CHF₂ —CH₂—CO—Ph 4-1130 Me Me Me Et 1 CHF₂ —CH₂—CO—Ph 4-1131 Me Me Men-Pr 1 CHF₂ —CH₂—CO—Ph 4-1132 Me Me Me Me 2 CHF₂ —CH₂—CO—Ph 4-1133 Me MeMe Et 2 CHF₂ —CH₂—CO—Ph 4-1134 Me Me Me n-Pr 2 CHF₂ —CH₂—CO—Ph

TABLE 5 Inventive compounds of the formula (IIIa),

No. X R¹ n Y Physical data: ¹H-NMR: δ [DMSO-d₆] 5-1 Me Me 0 CF₂Cl 5-2 MeEt 0 CF₂Cl 5-3 Me n-Pr 0 CF₂Cl 5-4 Me i-Pr 0 CF₂Cl 5-5 Me n-Bu 0 CF₂Cl5-6 Me i-Bu 0 CF₂Cl 5-7 Me s-Bu 0 CF₂Cl 5-8 Me t-Bu 0 CF₂Cl 5-9 Me Me 1CF₂Cl 5-10 Me Et 1 CF₂Cl 5-11 Me n-Pr 1 CF₂Cl 5-12 Me i-Pr 1 CF₂Cl 5-13Me n-Bu 1 CF₂Cl 5-14 Me i-Bu 1 CF₂Cl 5-15 Me s-Bu 1 CF₂Cl 5-16 Me t-Bu 1CF₂Cl 5-17 Me Me 2 CF₂Cl 5-18 Me Et 2 CF₂Cl 5-19 Me n-Pr 2 CF₂Cl 5-20 Mei-Pr 2 CF₂Cl 5-21 Me n-Bu 2 CF₂Cl 5-22 Me i-Bu 2 CF₂Cl 5-23 Me s-Bu 2CF₂Cl 5-24 Me t-Bu 2 CF₂Cl 5-25 Et Me 0 CF₂Cl 5-26 Et Et 0 CF₂Cl 5-27 Etn-Pr 0 CF₂Cl 5-28 Et i-Pr 0 CF₂Cl 5-29 Et n-Bu 0 CF₂Cl 5-30 Et i-Bu 0CF₂Cl 5-31 Et s-Bu 0 CF₂Cl 5-32 Et t-Bu 0 CF₂Cl 5-33 Et Me 1 CF₂Cl 5-34Et Et 1 CF₂Cl 5-35 Et n-Pr 1 CF₂Cl 5-36 Et i-Pr 1 CF₂Cl 5-37 Et n-Bu 1CF₂Cl 5-38 Et i-Bu 1 CF₂Cl 5-39 Et s-Bu 1 CF₂Cl 5-40 Et t-Bu 1 CF₂Cl5-41 Et Me 2 CF₂Cl 5-42 Et Et 2 CF₂Cl 5-43 Et n-Pr 2 CF₂Cl 5-44 Et i-Pr2 CF₂Cl 5-45 Et n-Bu 2 CF₂Cl 5-46 Et i-Bu 2 CF₂Cl 5-47 Et s-Bu 2 CF₂Cl5-48 Et t-Bu 2 CF₂Cl 5-49 Me Me 0 CFCl₂ 5-50 Me Et 0 CFCl₂ 5-51 Me n-Pr0 CFCl₂ 5-52 Me i-Pr 0 CFCl₂ 5-53 Me n-Bu 0 CFCl₂ 5-54 Me i-Bu 0 CFCl₂5-55 Me s-Bu 0 CFCl₂ 5-56 Me t-Bu 0 CFCl₂ 5-57 Me Me 1 CFCl₂ 5-58 Me Et1 CFCl₂ 5-59 Me n-Pr 1 CFCl₂ 5-60 Me i-Pr 1 CFCl₂ 5-61 Me n-Bu 1 CFCl₂5-62 Me i-Bu 1 CFCl₂ 5-63 Me s-Bu 1 CFCl₂ 5-64 Me t-Bu 1 CFCl₂ 5-65 MeMe 2 CFCl₂ 5-66 Me Et 2 CFCl₂ 5-67 Me n-Pr 2 CFCl₂ 5-68 Me i-Pr 2 CFCl₂5-69 Me n-Bu 2 CFCl₂ 5-70 Me i-Bu 2 CFCl₂ 5-71 Me s-Bu 2 CFCl₂ 5-72 Met-Bu 2 CFCl₂ 5-73 Et Me 0 CFCl₂ 5-74 Et Et 0 CFCl₂ 5-75 Et n-Pr 0 CFCl₂5-76 Et i-Pr 0 CFCl₂ 5-77 Et n-Bu 0 CFCl₂ 5-78 Et i-Bu 0 CFCl₂ 5-79 Ets-Bu 0 CFCl₂ 5-80 Et t-Bu 0 CFCl₂ 5-81 Et Me 1 CFCl₂ 5-82 Et Et 1 CFCl₂5-83 Et n-Pr 1 CFCl₂ 5-84 Et i-Pr 1 CFCl₂ 5-85 Et n-Bu 1 CFCl₂ 5-86 Eti-Bu 1 CFCl₂ 5-87 Et s-Bu 1 CFCl₂ 5-88 Et t-Bu 1 CFCl₂ 5-89 Et Me 2CFCl₂ 5-90 Et Et 2 CFCl₂ 5-91 Et n-Pr 2 CFCl₂ 5-92 Et i-Pr 2 CFCl₂ 5-93Et n-Bu 2 CFCl₂ 5-94 Et i-Bu 2 CFCl₂ 5-95 Et s-Bu 2 CFCl₂ 5-96 Et t-Bu 2CFCl₂ 5-97 Me Me 0 CCl₃ 5-98 Me Et 0 CCl₃ 5-99 Me n-Pr 0 CCl₃ 5-100 Mei-Pr 0 CCl₃ 5-101 Me n-Bu 0 CCl₃ 5-102 Me i-Bu 0 CCl₃ 5-103 Me s-Bu 0CCl₃ 5-104 Me t-Bu 0 CCl₃ 5-105 Me Me 1 CCl₃ 5-106 Me Et 1 CCl₃ 5-107 Men-Pr 1 CCl₃ 5-108 Me i-Pr 1 CCl₃ 5-109 Me n-Bu 1 CCl₃ 5-110 Me i-Bu 1CCl₃ 5-111 Me s-Bu 1 CCl₃ 5-112 Me t-Bu 1 CCl₃ 5-113 Me Me 2 CCl₃ 5-114Me Et 2 CCl₃ 5-115 Me n-Pr 2 CCl₃ 5-116 Me i-Pr 2 CCl₃ 5-117 Me n-Bu 2CCl₃ 5-118 Me i-Bu 2 CCl₃ 5-119 Me s-Bu 2 CCl₃ 5-120 Me t-Bu 2 CCl₃5-121 Et Me 0 CCl₃ 5-122 Et Et 0 CCl₃ 5-123 Et n-Pr 0 CCl₃ 5-124 Et i-Pr0 CCl₃ 5-125 Et n-Bu 0 CCl₃ 5-126 Et i-Bu 0 CCl₃ 5-127 Et s-Bu 0 CCl₃5-128 Et t-Bu 0 CCl₃ 5-129 Et Me 1 CCl₃ 5-130 Et Et 1 CCl₃ 5-131 Et n-Pr1 CCl₃ 5-132 Et i-Pr 1 CCl₃ 5-133 Et n-Bu 1 CCl₃ 5-134 Et i-Bu 1 CCl₃5-135 Et s-Bu 1 CCl₃ 5-136 Et t-Bu 1 CCl₃ 5-137 Et Me 2 CCl₃ 5-138 Et Et2 CCl₃ 5-139 Et n-Pr 2 CCl₃ 5-140 Et i-Pr 2 CCl₃ 5-141 Et n-Bu 2 CCl₃5-142 Et i-Bu 2 CCl₃ 5-143 Et s-Bu 2 CCl₃ 5-144 Et t-Bu 2 CCl₃ 5-145 MeMe 0 C₂F₅ 7.84 (d, 1H), 7.65 (d, 1H), 2.76 (s, 3H), 2.27 (s, 3H) 5-146Me Et 0 C₂F₅ 5-147 Me n-Pr 0 C₂F₅ 5-148 Me i-Pr 0 C₂F₅ 5-149 Me n-Bu 0C₂F₅ 5-150 Me i-Bu 0 C₂F₅ 5-151 Me s-Bu 0 C₂F₅ 5-152 Me t-Bu 0 C₂F₅5-153 Me Me 1 C₂F₅ 5-154 Me Et 1 C₂F₅ 5-155 Me n-Pr 1 C₂F₅ 5-156 Me i-Pr1 C₂F₅ 5-157 Me n-Bu 1 C₂F₅ 5-158 Me i-Bu 1 C₂F₅ 5-159 Me s-Bu 1 C₂F₅5-160 Me t-Bu 1 C₂F₅ 5-161 Me Me 2 C₂F₅ 8.03 (d, 1H), 7.82 (d, 1H), 3.44(s, 3H), 2.74 (s, 3H) 5-162 Me Et 2 C₂F₅ 5-163 Me n-Pr 2 C₂F₅ 5-164 Mei-Pr 2 C₂F₅ 5-165 Me n-Bu 2 C₂F₅ 5-166 Me i-Bu 2 C₂F₅ 5-167 Me s-Bu 2C₂F₅ 5-168 Me t-Bu 2 C₂F₅ 5-169 Et Me 0 C₂F₅ 5-170 Et Et 0 C₂F₅ 5-171 Etn-Pr 0 C₂F₅ 5-172 Et i-Pr 0 C₂F₅ 5-173 Et n-Bu 0 C₂F₅ 5-174 Et i-Bu 0C₂F₅ 5-175 Et s-Bu 0 C₂F₅ 5-176 Et t-Bu 0 C₂F₅ 5-177 Et Me 1 C₂F₅ 5-178Et Et 1 C₂F₅ 5-179 Et n-Pr 1 C₂F₅ 5-180 Et i-Pr 1 C₂F₅ 5-181 Et n-Bu 1C₂F₅ 5-182 Et i-Bu 1 C₂F₅ 5-183 Et s-Bu 1 C₂F₅ 5-184 Et t-Bu 1 C₂F₅5-185 Et Me 2 C₂F₅ 5-186 Et Et 2 C₂F₅ 5-187 Et n-Pr 2 C₂F₅ 5-188 Et i-Pr2 C₂F₅ 5-189 Et n-Bu 2 C₂F₅ 5-190 Et i-Bu 2 C₂F₅ 5-191 Et s-Bu 2 C₂F₅5-192 Et t-Bu 2 C₂F₅ 5-193 Me Me 0 CF(CF₃)₂ 5-194 Me Et 0 CF(CF₃)₂ 5-195Me n-Pr 0 CF(CF₃)₂ 5-196 Me i-Pr 0 CF(CF₃)₂ 5-197 Me n-Bu 0 CF(CF₃)₂5-198 Me i-Bu 0 CF(CF₃)₂ 5-199 Me s-Bu 0 CF(CF₃)₂ 5-200 Me t-Bu 0CF(CF₃)₂ 5-201 Me Me 1 CF(CF₃)₂ 5-202 Me Et 1 CF(CF₃)₂ 5-203 Me n-Pr 1CF(CF₃)₂ 5-204 Me i-Pr 1 CF(CF₃)₂ 5-205 Me n-Bu 1 CF(CF₃)₂ 5-206 Me i-Bu1 CF(CF₃)₂ 5-207 Me s-Bu 1 CF(CF₃)₂ 5-208 Me t-Bu 1 CF(CF₃)₂ 5-209 Me Me2 CF(CF₃)₂ 5-210 Me Et 2 CF(CF₃)₂ 5-211 Me n-Pr 2 CF(CF₃)₂ 5-212 Me i-Pr2 CF(CF₃)₂ 5-213 Me n-Bu 2 CF(CF₃)₂ 5-214 Me i-Bu 2 CF(CF₃)₂ 5-215 Mes-Bu 2 CF(CF₃)₂ 5-216 Me t-Bu 2 CF(CF₃)₂ 5-217 Et Me 0 CF(CF₃)₂ 5-218 EtEt 0 CF(CF₃)₂ 5-219 Et n-Pr 0 CF(CF₃)₂ 5-220 Et i-Pr 0 CF(CF₃)₂ 5-221 Etn-Bu 0 CF(CF₃)₂ 5-222 Et i-Bu 0 CF(CF₃)₂ 5-223 Et s-Bu 0 CF(CF₃)₂ 5-224Et t-Bu 0 CF(CF₃)₂ 5-225 Et Me 1 CF(CF₃)₂ 5-226 Et Et 1 CF(CF₃)₂ 5-227Et n-Pr 1 CF(CF₃)₂ 5-228 Et i-Pr 1 CF(CF₃)₂ 5-229 Et n-Bu 1 CF(CF₃)₂5-230 Et i-Bu 1 CF(CF₃)₂ 5-231 Et s-Bu 1 CF(CF₃)₂ 5-232 Et t-Bu 1CF(CF₃)₂ 5-233 Et Me 2 CF(CF₃)₂ 5-234 Et Et 2 CF(CF₃)₂ 5-235 Et n-Pr 2CF(CF₃)₂ 5-236 Et i-Pr 2 CF(CF₃)₂ 5-237 Et n-Bu 2 CF(CF₃)₂ 5-238 Et i-Bu2 CF(CF₃)₂ 5-239 Et s-Bu 2 CF(CF₃)₂ 5-240 Et t-Bu 2 CF(CF₃)₂ 5-241 Me Me0 CHF₂ 5-242 Me Et 0 CHF₂ 5-243 Me n-Pr 0 CHF₂ 5-244 Me i-Pr 0 CHF₂5-245 Me n-Bu 0 CHF₂ 5-246 Me i-Bu 0 CHF₂ 5-247 Me s-Bu 0 CHF₂ 5-248 Met-Bu 0 CHF₂ 5-249 Me Me 1 CHF₂ 5-250 Me Et 1 CHF₂ 5-251 Me n-Pr 1 CHF₂5-252 Me i-Pr 1 CHF₂ 5-253 Me n-Bu 1 CHF₂ 5-254 Me i-Bu 1 CHF₂ 5-255 Mes-Bu 1 CHF₂ 5-256 Me t-Bu 1 CHF₂ 5-257 Me Me 2 CHF₂ 5-258 Me Et 2 CHF₂5-259 Me n-Pr 2 CHF₂ 5-260 Me i-Pr 2 CHF₂ 5-261 Me n-Bu 2 CHF₂ 5-262 Mei-Bu 2 CHF₂ 5-263 Me s-Bu 2 CHF₂ 5-264 Me t-Bu 2 CHF₂ 5-265 Et Me 0 CHF₂5-266 Et Et 0 CHF₂ 5-267 Et n-Pr 0 CHF₂ 5-268 Et i-Pr 0 CHF₂ 5-269 Etn-Bu 0 CHF₂ 5-270 Et i-Bu 0 CHF₂ 5-271 Et s-Bu 0 CHF₂ 5-272 Et t-Bu 0CHF₂ 5-273 Et Me 1 CHF₂ 5-274 Et Et 1 CHF₂ 5-275 Et n-Pr 1 CHF₂ 5-276 Eti-Pr 1 CHF₂ 5-277 Et n-Bu 1 CHF₂ 5-278 Et i-Bu 1 CHF₂ 5-279 Et s-Bu 1CHF₂ 5-280 Et t-Bu 1 CHF₂ 5-281 Et Me 2 CHF₂ 5-282 Et Et 2 CHF₂ 5-283 Etn-Pr 2 CHF₂ 5-284 Et i-Pr 2 CHF₂ 5-285 Et n-Bu 2 CHF₂ 5-286 Et i-Bu 2CHF₂ 5-287 Et s-Bu 2 CHF₂ 5-288 Et t-Bu 2 CHF₂

B. Formulation Examples

1. Dust

A dust is obtained by mixing 10 parts by weight of a compound of theformula (I) and 90 parts by weight of talc as inert substance andcomminuting the mixture in a hammer mill.

2. Dispersible Powder

A wettable powder which is readily dispersible in water is obtained bymixing 25 parts by weight of a compound of the formula (I), 64 parts byweight of kaolin-containing quartz as inert substance, 10 parts byweight of potassium lignosulfonate and 1 part by weight of sodiumoleoylmethyltaurinate as wetting agent and dispersant, and grinding themixture in a pinned-disk mill.

3. Dispersible Concentrate

A readily water-dispersible dispersion concentrate is obtained by mixing20 parts by weight of a compound of the formula (I) with 6 parts byweight of alkylphenol polyglycol ether (®Triton X 207), 3 parts byweight of isotridecanol polyglycol ether (8 EO) and 71 parts by weightof paraffinic mineral oil (boiling range for example about 255 to above277° C.) and grinding the mixture in a ball mill to a fineness of below5 microns.

4. Emulsifiable Concentrate

An emulsifiable concentrate is obtained from 15 parts by weight of acompound of the formula (I), 75 parts by weight of cyclohexanone assolvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.

5. Water-Dispersible Granules

-   Water-dispersible granules are obtained by mixing-   75 parts by weight of a compound of the formula (I),-   10 parts by weight of calcium lignosulfonate,-   5 parts by weight of sodium lauryl sulfate,-   3 parts by weight of polyvinyl alcohol and-   7 parts by weight of kaolin,-   grinding the mixture in a pinned-disk mill, and granulating the    powder in a fluidized bed by spraying on water as granulating    liquid.

Water-dispersible granules are also obtained by homogenizing andprecomminuting, in a colloid mill,

-   25 parts by weight of a compound of the formula (I),-   5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,-   2 parts by weight of sodium oleoylmethyltaurinate,-   1 part by weight of polyvinyl alcohol,-   17 parts by weight of calcium carbonate and-   50 parts by weight of water,    subsequently grinding the mixture in a bead mill and atomizing and    drying the resulting suspension in a spray tower by means of a    single-fluid nozzle.

C. Biological Examples

1. Pre-Emergence Herbicidal Action Against Weed Plants

Seeds or rhizome sections of mono- and dicotyledonous weed plants areset out in pots of 9 to 13 cm in diameter, in sandy loam soil, and arecovered with soil. The herbicides, formulated as emulsifiableconcentrates or dusts, are applied to the surface of the covering earthin the form of aqueous dispersions or suspensions or emulsions, at awater application rate of 300 to 800 I/ha (converted) in differentdoses. The pots are then maintained under glass under optimum conditionsfor the further cultivation of the plants. After 3 to 4 weeks underoptimum growth conditions under glass, the trial plants are scored forthe effect of the compounds according to the invention in comparison tocompounds disclosed in the prior art. As the results in the comparisontables show, the selected compounds according to the invention exhibit abetter herbicidal activity against a broad spectrum of economicallyimportant monocotyledonous and dicotyledonous weeds than the compoundsdisclosed in the prior art.

The meanings of the abbreviations used in the comparison tables beloware as follows:

ALOMY Alopecurus AMARE Amaranthus myosuroides retroflexus AVEFA Avenafatua CYPES Cyperus serotinus MATIN Matricaria inodora SETVI Setariaviridis VIOTR Viola tricolor

Comparison table 1: Pre-emergence Herbicidal action against CompoundDose [g a.c./ha] AVEFA CYPES VIOTR

80 70% 100% 90% inventive compound No. 1-153

80 40%  50% 60% compound No. 1-9, known from WO 2008/125214

Comparison table 2: Pre-emergence Dose Herbicidal [g a.c./ actionagainst Compound ha] ALOMY CYPES

320 90% 80% inventive compound No. 3-161

320 50% 50% compound No. 3-17, known from WO 2008/125214

Comparison table 3: Pre-emergence Herbicidal Dose action againstCompound [g a.c./ha] VIOTR

320 90% inventive compound No. 3-153

320 40% compound No. 3-9, known from WO 2008/1252142. Post-Emergence Herbicidal Action Against Weed PlantsSeeds of monocotyledonous and dicotyledonous weed plants are set out incardboard pots in sandy loam soil, covered with soil, and cultivatedunder glass under good growth conditions. Two to three weeks aftersowing, the trial plants are treated at the three-leaf stage. Thecompounds according to the invention, formulated as wettable powders oras emulsifiable concentrates, are sprayed onto the surface of the greenparts of the plants, at a water application rate of 600 to 800 I/ha(converted). After the trial plants have stood for 3 to 4 weeks underoptimum growth conditions under glass, the action of the compoundsaccording to the invention is scored in comparison to compoundsdisclosed in the prior art. As the results in the comparison tablesshow, the selected compounds according to the invention exhibit a betterherbicidal activity against a broad spectrum of economically importantmonocotyledonous and dicotyledonous weeds than the compounds disclosedin the prior art.

Comparison table 4: Post-emergence Herbicidal Dose action againstCompound [g a.c./ha] MATIN

80 100% inventive compound No. 1-161

80  50% compound No. 1-4, known from WO 2008/125214

Comparison table 5: Post-emergence Dose Herbicidal [g a.c./ actionagainst Compound ha] AMARE VIOTR

320 80% 80% inventive compound No. 3-153

320 50% 40% compound No. 3-9, known from WO 2008/125214

Comparison table 6: Post-emergence Herbicidal Dose action againstCompound [g a.c./ha] SETVI

80 100% inventive compound No. 3-161

80  60% compound No. 3-17, known from WO 2008/125214

What is claimed is:
 1. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole offormula (I) and/or salt thereof

in which X is (C₁-C₄)-alkyl, Y is (C₁-C₄)-haloalkyl, R¹ is(C₁-C₄)-alkyl, R² is (C₁-C₄)-alkyl, R³ is hydrogen or (C₁-C₄)-alkyl, R⁴is hydrogen, (C₁-C₆)-alkylsulfonyl,(C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl,thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl, each ofwhich is substituted by m identical or different radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, and (C₁-C₄)-alkoxy, m is 0, 1, 2or 3, and n is 0, 1 or 2, with the proviso that Y is nottrifluoromethyl.
 2. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or saltas claimed in claim 1, in which X is (C₁-C₄)-alkyl, Y is(C₁-C₄)-haloalkyl, R^(l) is (C₁-C₄)-alkyl, R² is (C₁-C₄)-alkyl, R³ ishydrogen or (C₁-C₄)-alkyl, R⁴ is hydrogen, (C₁-C₆)-alkylsulfonyl,(C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, or is phenylsulfonyl,thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl or benzyl, each ofwhich is substituted by m identical or different radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, and (C₁-C₄)-alkoxy, m is 0, 1, 2or 3, and n is 0, 1 or 2, with the proviso that Y is nottrifluoromethyl.
 3. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or saltas claimed in claim 1, in which X is (C₁-C₄)-alkyl, Y istrichloromethyl, difluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, pentafluoroethyl or heptafluoroisopropyl, R¹ is(C₁-C₄)-alkyl, R² is (C₁-C₄)-alkyl, R³ is hydrogen or (C₁-C₄)-alkyl, R⁴is hydrogen, n-propylsulfonyl, methoxyethylsulfonyl, phenylsulfonyl,4-methyl -phenylsulfonyl, or thiophenyl-2-sulfonyl, and n is 0, 1 or 2.4. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or salt as claimed inclaim 1, in which X is methyl, Y is difluoromethyl or pentafluoroethyl,R¹ is methyl, R² is methyl, R³ is hydrogen or methyl, R⁴ is hydrogen,and n is 1 or
 2. 5. A 4-(4-haloalkyl-3-thiobenzoyl)pyrazole and/or saltas claimed in claim 1, in which X is methyl, Y is pentafluoroethyl, R¹is methyl, R² is methyl, R³ is hydrogen or methyl, R⁴ is hydrogen, and nis 1 or
 2. 6. A herbicidal composition which comprises a herbicidallyeffective amount of at least one compound as claimed in claim
 1. 7. Theherbicidal composition as claimed in claim 6 in a mixture with at leastone formulation auxiliary.
 8. The herbicidal composition as claimed inclaim 6, comprising at least one further pesticidally active compoundfrom the group of insecticides, acaricides, herbicides, fungicides,safeners, and growth regulators.
 9. The herbicidal composition asclaimed in claim 6, comprising a safener.
 10. The herbicidal compositionas claimed in claim 6, comprising a further herbicide.
 11. A method forcontrolling unwanted plants, which comprises applying an effectiveamount of at least one compound as claimed in claim 1 to plants and/orto a location of unwanted plant growth.
 12. A herbicidal composition asclaimed in claim 6 which is capable of controlling unwanted plants. 13.The composition as claimed in claim 12, wherein the compound of formula(I) and/or salt is capable of controlling unwanted plants in crops ofuseful plants.
 14. The composition as claimed in claim 13, wherein theuseful plants are transgenic useful plants.
 15. A method for controllingunwanted plants, which comprises applying an effective amount of atleast one compound as claimed in claim 2 to plants and/or to a locationof unwanted plant growth.
 16. A method for controlling unwanted plants,which comprises applying an effective amount of at least one compound asclaimed in claim 3 to plants and/or to a location of unwanted plantgrowth.
 17. A method for controlling unwanted plants, which comprisesapplying an effective amount of at least one compound as claimed inclaim 4 to plants and/or to a location of unwanted plant growth.
 18. Amethod for controlling unwanted plants, which comprises applying aneffective amount of at least one compound as claimed in claim 5 toplants and/or to a location of unwanted plant growth.